Reaction #1261

Reaction equation

(-)-2-(4-(3-hydroxy-1-butenyl)phenyl)-5-decyloxypyrimidine

butyryl chloride

→

(+)-2-(4-(3-butyryloxy-1-butenyl)phenyl)-5-decyloxy-pyrimidine

Yield 88.7%

Solvents

toluene

pyridine

Conditions

Workup

1. 1
   Washwashed with 4N hydrochloric acid, water
2. 2
   ConcentrationThe toluene layer was concentrated under reduced pressure
3. 3
   Otherthe residue was purified by silica gel column chromatography

Procedure

1.0 g of (-)-2-(4-(3-hydroxy-1-butenyl)phenyl)-5-decyloxypyrimidine was dissolved in 20 ml of pyridine, added with 0.5 g of butyryl chloride and stirred at 25°-30° C. for 4 hours. The reaction mixture was diluted with 100 ml of toluene and washed with 4N hydrochloric acid, water, a 5% sodium bicarbonate solution and water successively in that order. The toluene layer was concentrated under reduced pressure and the residue was purified by silica gel column chromatography using toluene/ethyl acetate as eluent to obtain 1.05 g of (+)-2-(4-(3-butyryloxy-1-butenyl)phenyl)-5-decyloxy-pyrimidine.

Source