1. Synthesis of Diethyl Benzyloxy-Methyl-Malonate (Ergovaline)

all right well I'm going to try to weigh

out three point nine six five grams of

60% sodium hydride this stuff that's

eaten away at the plastic bag that was

originally in quite a bit but I think

it's still good


I can try not to get plastic pieces in


right close them I did heat this with a

heat gun so it should be relatively dry

but I am going to open it to throw this

in here three point nine nine three

grams and this one I'm running two of

them so it's going to do it again the

only reason I'm running to is click

don't have a two liter flask and I only

have one liter left this way if I screw

up on one least I have the other ones in

it but I am making it double to work all

right should be in there close enough to

three point nine six five there is a

little bit of those yellow plastic


hopefully won't matter too much just to

make sure the sodium hydride is still

good and some water here I have a little

bit of it still stuck on this so still

good should react looks pretty good to

me right now I'm just going to add 250

no leader of toluene through each of

these left

I will now add about ten point three

milliliters of benzyl alcohol

I do see some bubbles so maybe

something's happening but it's hard to

tell it's just kind of stirring or

reacting all right looks like it's all

added I'll do the same thing for this

flash this one certainly looks like it's

reacting more this one bubbling up quite

a bit how do you even see it so white

Wow I wonder why this one foaming so

much and the other one did all right

that one's done as well now to this one

mole equivalent of the benzyl alcohol

are approximately 1 mol equivalent

relative to the sodium hydride there

this one's still going good this one

doesn't look like it's foaming at all

this one all sorts of puzzles all right

so now I'm going to hook up condensers

to each of them so I can reflux them for

an hour make sure it does go to


Wow yes yes

all right just turn down the water so

the condenser looks like that's working

out okay the layers are set up I just

have drying shoot at the top of the

condensers I did take a heat gun ahead

of time and I did try to get rid of the

water as much as I could from the

condensers and the drying tube now I'll

just get it to reflux all right so it's

only it's been about 10 minutes maybe 15

at the most this oil baths up to 81 this

one's at 68 both of these solutions are

looking a little funny for its color

they both look tan or brown light brown

I don't know I guess can - better

stripped it for it

this shouldn't be because the salt

itself is white and I'm guessing it's

this color just because of those little

plastic pieces which were discolored

actually but I mean there's little

chunks in there that

that looks like they're red or black I'm

I'm hoping that's what's influencing the

color here and it's just a small amount

color doesn't necessarily mean a whole

lot so hopefully everything will still

work out all right so it's only been a

few more minutes maybe 25 minutes total

and this one is boiling already it's at

99 degrees Celsius

you see it's becoming very gel-like and

can't even see it really stirring


looks like the condensers working fine

only have some condensate up this far

nothing higher than that another

solution is at 84 degrees Celsius not

quite boiling yet not quite solidified

yet if you have some stuff that looks

like it got up here though

the condenser too as well working just

fine it looks like the condensate the

farthest got to the bunch of this line

been about an hour since they both

started to reflux

he's only this one started a little bit

earlier I'm going to go ahead and stop

them both this one did start spinning

again and it looks like it's a little

bit less viscous now this one is really

spinning well hopefully everything's

okay still seems like there's a lot of

salt there it's just not as

biscuit as I thought it would be

this one certainly has a lot more it

would seem but anyway stop them both let

them cool down to room temperature I'll

throw them in some ice

all right they both should be cooled now

in the ice water bath

and now I'm going to add on 18.9 Mills

are 25 grams of the diethyl bromo methyl

melanie can't really see anything


if it was a big solid clump it should

start dissolving as this is added but

since it's already stirring well can't

really tell although it does seem to be

doing better and better as I add this

fill most becoming transparent

looking pretty good at that I can almost

see the stir bar again alright that's

the last of it look at that

not bad remember it looked like this so

I'll go ahead and least take this out of

the ice water bath for now completely

transparent now no salt at all left

anymore which is a pretty good sign as

you can do the same thing with this one

this one still has some salt up here but

I will keep this

all right there we go the condensers are

hooked back up and now I'm just going to

heat it to about 70 degrees Celsius for

four hours

all right been four hours since the

temperature has been between somewhere

between 60 and looks like the highest

now it's been at this one seventy one

point six this one is at six to nine

point seven that's probably as high as

temperature too but anyway between 60

degrees and 72 degrees Celsius for at

least four hours mostly around 65 I'm

going to go ahead and quench this with

20 mils of water look at all that salt


all right so go ahead and transfer it

over to the secretory cell oh I dropped

the stir bar in there

have a little toluene here and skin

rinse this out once anyway so I'll be

able to wash back whatever little amount

for that hat stir bar

there's certainly two layers there I

thought about adding some more water to

dissolve this but I don't think I need

to I think it's just going to come out

with the water layer for the most part

I still had more water this time I got

measured at 35 milliliters

then I will collect let's call you mean

that should have my product in it as


now hopefully it'll clear itself up to

get rid of that water

doesn't look like it's going to do the


sorry I'm Kennedy Kansas in 2000 middle



still kind of a free-flowing liquid in

there alright so I'm going to drive


doesn't look like it's very wet because

the sodium sulfate did not come up at

all so that's a good sign

it is so cloudy though probably because

the toluene I guess that's okay I need

to transfer it to another flask anyway

when I would just use dichloromethane

this time

looking pretty clear now

all right so here they both are should

be completely wrote a bath down they

both don't smell like any solvents they

smell sweet like a obn should this one I

have 27 point one seven one gram and the

other one twenty seven point nine three

four grams so the proton is done

there it is

here's a triplet for the two ch3 groups

off the ethyl ester here's the

corresponding quartet for the two ch2

groups here is the singlet or the methyl

group here's the singlet for the ch2

from the spindle oxy and here are the

five aromatic hydrogen