반응 #51639

반응 방정식

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

용매

water

ethanol

THF

ethanol water

반응 조건

후처리

1. 1
   온도to warm to room temperature
2. 2
   workup.STIRRINGstirred overnight
3. 3
   기타The organic solvents were removed in vacuo under a stream of nitrogen
4. 4
   workup.ADDITIONthe residue was diluted with water (50 mL)
5. 5
   추출extracted with methylene chloride (3×)
6. 6
   세척The organic fractions were washed with water (2×), brine (1×)
7. 7
   여과filtered through sodium sulfate
8. 8
   농축concentrated in vacuo
9. 9
   기타The residue was triturated with ether

실험 절차

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%.

출처