تفاعل #51639

معادلة التفاعل

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

المذيبات

water

ethanol

THF

ethanol water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto warm to room temperature
2. 2
   workup.STIRRINGstirred overnight
3. 3
   أخرىThe organic solvents were removed in vacuo under a stream of nitrogen
4. 4
   workup.ADDITIONthe residue was diluted with water (50 mL)
5. 5
   استخلاصextracted with methylene chloride (3×)
6. 6
   غسيلThe organic fractions were washed with water (2×), brine (1×)
7. 7
   ترشيحfiltered through sodium sulfate
8. 8
   تركيزconcentrated in vacuo
9. 9
   أخرىThe residue was triturated with ether

الإجراء التجريبي

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%.

المصدر