反応 #51639

反応方程式

acetic acid

diacetate

2-Methoxy-3,17-diacetoxyestra-1,3,5(10),14,16-pentaene

sodium borohydride

→

product ( 18 )

2-Methoxyestra-1,3,5(10),14-tetraen-3,17β-diol

溶媒

water

ethanol

THF

ethanol water

反応条件

後処理

1. 1
   温度to warm to room temperature
2. 2
   workup.STIRRINGstirred overnight
3. 3
   その他The organic solvents were removed in vacuo under a stream of nitrogen
4. 4
   workup.ADDITIONthe residue was diluted with water (50 mL)
5. 5
   抽出extracted with methylene chloride (3×)
6. 6
   洗浄The organic fractions were washed with water (2×), brine (1×)
7. 7
   ろ過filtered through sodium sulfate
8. 8
   濃縮concentrated in vacuo
9. 9
   その他The residue was triturated with ether

実験手順

A solution of the diacetate (17) (0.08 g, 0.21 mmol) in ethanol (5 mL) and THF (3 mL) was cooled to 0° C. in an ice bath. A solution of sodium borohydride (0.05 g, 1.32 mmol) in ethanol/water (10:3, 5 mL) was cooled to 0° C. in an ice bath and added to the steroid solution. The reaction mixture was stirred at 0° C. for 1 h., then allowed to warm to room temperature and stirred overnight. After that time, the reaction was diluted with water (20 mL) and neutralized with glacial acetic acid. The organic solvents were removed in vacuo under a stream of nitrogen, the residue was diluted with water (50 mL) and extracted with methylene chloride (3×). The organic fractions were washed with water (2×), brine (1×), filtered through sodium sulfate, combined and concentrated in vacuo. The residue was triturated with ether to give the pure product (18) (0.035 g, 55.7%.

出典