反応 #2025283

反応方程式

butyrylchloride

(+)-3-methyl-3-(4-benzyloxyphenyl)propanol

water

→

(+)-4-benzyloxy-1-(1-methyl-3-butyryloxypropyl)benzene

収率 95.0%

溶媒

pyridine

反応条件

後処理

1. 1
   その他reacted for 2 hours
2. 2
   抽出extracted with 200 ml of toluene
3. 3
   その他separated
4. 4
   洗浄washed with, in the order, 1N aqueous solution of hydrochloric acid, water, 5% aqueous solution of sodium bicarbonate and water
5. 5
   乾燥dried on anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONAfter the solvent was distilled out under the reduced pressure
7. 7
   その他the resulting residue was purified by silica gel column chromatography (eluent: toluene-ethyl acetate)

実験手順

2.56 (10 millimols) of (+)-3-methyl-3-(4-benzyloxyphenyl)propanol (XI-1) obtained in Preparation Example (starting material compound (V)) 1, was dissolved in 20 ml of pyridine and 1.38 g (13 millimols) of butyrylchloride was added at 30°-40° C. and reacted for 2 hours. The reaction mixture was poured into 200 ml of water and extracted with 200 ml of toluene and separated and then washed with, in the order, 1N aqueous solution of hydrochloric acid, water, 5% aqueous solution of sodium bicarbonate and water, and thereafter dried on anhydrous magnesium sulfate. After the solvent was distilled out under the reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent: toluene-ethyl acetate) to provide 3.1 g (yield: 95%) of (+)-4-benzyloxy-1-(1-methyl-3-butyryloxypropyl)benzene (VIII-9).

出典