反応 #82145

反応方程式

ether

acetic anhydride

morphine

→

3-acetylmorphine

収率 80.0%

溶媒

sodium bicarbonate

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   抽出the solution was extracted with dichloromethane (200 ml)
3. 3
   抽出The organic extract
4. 4
   洗浄was washed with brine
5. 5
   乾燥dried over Na2SO4
6. 6
   その他the solvent removed in vacuo
7. 7
   その他to leave a sticky white residue

実験手順

To a stirred suspension of morphine (4 g, 14 mmol) in 10% aqueous sodium bicarbonate (377 ml) was added acetic anhydride (19 ml) over 8.5 minutes. 15 minutes after the addition, ice cold water (300 ml) was added and the solution was extracted with dichloromethane (200 ml). The organic extract was washed with brine, dried over Na2SO4, and the solvent removed in vacuo to leave a sticky white residue. Trituration with ether gave 3-acetylmorphine (3.68 g, 80%). The corresponding 3-pivalyl, 3-isobutyryl, 3-propionyl and other 3-acyl derivatives of morphine were also prepared.

出典