           Base-catalyzed hydrolysis of ergocristine to lysergic acid
                                     by KrZ

Ergocristine base was obatined, and the subsequent base-catalyzed hydrolysis was
a glowing success.  The procedure here is very simple.  Gloves should be worn at
all times.  Have a bucket of water to rinse the gloves in before you take them
off so you will not contact the skin when trying to remove them, be careful
cleaning all glassware.

Placed into a 1L flask;
33.5g KOH
500mL dH2O

The flask was stirred magnetically, heating was commenced and the temperature of
the solution was allowed to reach 75C.  50g of Ergocristine base was added in 2g
fractions over a period of 30 minutes.  The mix went from clear to a light
golden yellow tint over the course of the addition.  Everything was in solution
after 50 minutes.  The reaction was allowed to proceed for a total of 5 hours
after complete addition.  Heating was removed and the reaction flask placed in a
room temp. water bath, and then in an ice bath, until the solution was at 5C.
325 mL 2.5 N H2SO4 was placed in an addition funnel, the flask placed in the
ice-bath and stirred, and the acid was added dropwise.  As the volume added
reached ~200 mL pH metering was commenced, and addition was halted when the pH
reached 3.0, ~50 mL of acid remained in the addition funnel.  The flask was
sprayed out with a stream of nitrogen, stoppered, wrapped in aluminum foil, and
stored at 0C for 18 hours (dark, of course).  The flask was then removed,
swirled vigorously to mix the solids, and quickly poured onto the buchner
funnel.  100 mL of Et2O was added to the flask, in two fractions, swirled, and
poured over the filter cake.  The filter cake was placed in a vacuum dessicator
in the dark for two hours. The filter cake was scraped into 500 mL NH3/EtOH
solution, and the filter paper rinsed with two syringes full of the NH3/EtOH
solution.  The solution was stirred for 90 minutes (lights off), decanted, the
solids re-extracted with a second 500 mL NH3/EtOH fraction (90 min. stirring,
lights off), and filtered to remove the remaing solids (weight 1440 mg).  The
pooled extracts were stripped of solvent under vacuum at the rotovap (lights
off, temp. set then left in dark).  The solids remaing in the flask were taken
up in 500 mL of 1% Aq. Ammonia.  250 mL 2.5 N H2SO4 was placed in the addition
funnel, and added slowly with stirring to a beaker containing the extract.  The
pH was monitored continuously and addition was halted as the pH reached 3.0, the
beaker was covered and placed in the refrigerator overnight.  The solids were
stirred vigorously to suspend them and collected by vacuum filtration.
The beaker was swirled with 100 mL Et2O and the briefly suspended solids poured
over the filter cake.  The filter cake was placed in the vacuum dessicator for
two hours (in the dark), and then weighed at 16.48g, placed in a brown glass
vial, sprayed with nitrogen, sealed, wrapped in foil, and stored in the freezer
at -10C. The yield equates to 73%.

15% NH3 in EtOH prep.

1000 mL of 15% Ammonia in Anhydrous Ethanol was prepared by the slow addition of
NaOH to cold absolute ethanol containg NH4Cl (not dissolved), filtration, and
drying of the formed water by adding 0.20g CaO/1g H2O formed, with stirring and
cooling.  The formed calcium hydroxide was filtered.

Lighting

Regular lighting was used during the reaction.  Two red photography lights were
used during the reaction workup.

