Ethyl vinyl ether → HCID 14882760, compound

HRID 329359Notes

Reaction equation

HRID 329359 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:11](=[CH:12][CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[OH:28])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:29](OC=C)[CH3:30]>>[Si:1]([O:8][C@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:11](=[CH:12][CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[O:28][CH:29]=[CH2:30])[CH2:10]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 8023Ethyl vinyl etherHCID 11069504HCID 11069504, compound

Product 1

HCID 14882760HCID 14882760, compound

Procedure

To a solution of 4 g of 3β-(t-butyldimethylsilyloxy)androst-5-en-17β-ol in 50 ml of vinyl ethyl ether, there was added 0.25 g of mercuric acetate. The mixture was stirred at room temperature for 24 hours, quenched with triethylamine, and then poured into dilute aqueous potassium carbonate solution. The aqueous mixture was extracted 3 times with 100 ml-portions of diethyl ether and the combined organic extracts were washed with saturated aqueous sodium chloride solution and then dried over sodium sulfate. The solvent was then removed under reduced pressure and the residue was purified by flash chromatography using ethyl acetate/hexane, 1:4, to give 3β-(t-butyldimethylsilyloxy)-17β-ethenyloxyandrost-5-ene.

Workup

  1. customquenched with triethylamine
  2. additionpoured into dilute aqueous potassium carbonate solution
  3. extractionThe aqueous mixture was extracted 3 times with 100 ml-portions of diethyl ether
  4. washthe combined organic extracts were washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was then removed under reduced pressure
  7. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-ea27c64b029c45fdaad29f872e2f5a32
Source dataset
uspto-grants-1990_01
Patent number
US04891367

Reaction notes

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