Ethyl vinyl ether → HCID 15085895, compound

HRID 1089424Notes

Reaction equation

HRID 1089424 reaction equation
[F:1][C:2]1([F:29])[C@@H:19]([O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[CH2:18][CH2:17][C@@:16]2([CH3:27])[C:3]1=[CH:4][CH2:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[OH:28].[CH2:30](OC=C)[CH3:31]>>[F:29][C:2]1([F:1])[C@@H:19]([O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[CH2:18][CH2:17][C@@:16]2([CH3:27])[C:3]1=[CH:4][CH2:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[O:28][CH:30]=[CH2:31]

Participants

3

Reactant 2

HCID 8023Ethyl vinyl etherHCID 15085894HCID 15085894, compound

Product 1

HCID 15085895HCID 15085895, compound

Procedure

To a solution of 4 g of 4,4-difluoro-3β-(2-tetrahydropyranyloxy)androst-5-en-17β-ol in 50 ml of vinyl ethyl ether, there is added 0.25 g of mercuric acetate. The mixture is stirred at room temperature for 24 hours, quenched with triethylamine, and then poured into dilute aqueous potassium carbonate solution. The aqueous mixture is extracted three times with 100-ml portions of diethyl ether and the combined organic extracts are washed with saturated aqueous sodium chloride solution and then dried over sodium sulfate. The solvent is then removed under reduced pressure and the residue is purified by flash chromatography to give 4,4-difluoro-3β-(2-tetrahydropyranyloxy)-17β-ethenyloxyandrost-5-ene.

Workup

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

Sources & evidence

ORD record
ord-1c06a5f097b545b2ad929a05842f2be9
Source dataset
uspto-grants-1990_10
Patent number
US04966897

Reaction notes

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