تفاعل #319977

معادلة التفاعل

3α-hydroxy-5α-androstan-17-one

dimethylformamide

imidazole

t-butyldimethylsilylchloride

→

titled compound

المردود 91.1%

3α-t-butyldimethylsilyloxy-5α-androstan-17-one

المردود 91.1%

المذيبات

pyridine

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction mixture was then partitioned between 220 mL of water and 220 mL of ethyl acetate
2. 2
   غسيلthe combined organic layers were washed with water
3. 3
   تجفيفdried over anhydrous sodium sulfate
4. 4
   أخرىThe solvent was removed in vacuo and absolute ethanol
5. 5
   workup.ADDITIONwas added

الإجراء التجريبي

To 3α-hydroxy-5α-androstan-17-one (25.22 g, 290.5 g/mol, 86.8 mmol) dissolved in 65 mL of dry pyridine was added 65 mL of dry dimethylformamide, imidazole (14.77 g, 68.1 g/mol, 217 mmol), and t-butyldimethylsilylchloride (16.36 g, 151 g/mol, 109 mmol), and the reaction was allowed to stand at room temperature for 12 hours. The reaction mixture was then partitioned between 220 mL of water and 220 mL of ethyl acetate and the combined organic layers were washed with water and dried over anhydrous sodium sulfate. The solvent was removed in vacuo and absolute ethanol was added with cooling to -20° C. to give the titled compound (32 g, 91% yield).

المصدر