Imidazole → HCID 131719415, compound

HRID 440722Notes

Reaction equation

HRID 440722 reaction equation
[OH:1][CH2:2][CH2:3][S:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[O:24])[CH2:6]1.N1C=CN=C1.[Si:30](Cl)([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31].O>CN(C)C=O>[Si:30]([O:1][CH2:2][CH2:3][S:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[O:24])[CH2:6]1)([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 54115112HCID 54115112, compound

Product 1

HCID 131719415HCID 131719415, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.0 g of 3β-(2-hydroxyethylthio)-androst-5-en-17-one in 20 ml of dimethylformamide, 1.7 g of imidazole and 2.0 g of t-butyldimethylsilyl chloride were added at 0° C. After 12 hrs the mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure to give 1.2 g of crude 3β-(2-tert-butyldimethylsilyloxyethythio)-androst-5-en-17-one.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-476d17fa51444200b59d417e93898e0a
Source dataset
uspto-grants-1996_05
Patent number
US05521167

Reaction notes

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