Ethyl vinyl ether → HCID 69282804, compound

HRID 1267141Notes

Reaction equation

HRID 1267141 reaction equation
[CH3:1][C:2]([Si:5]([CH3:33])([CH3:32])[O:6][CH2:7][C@@H:8]([CH3:31])[C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([C:17]([CH3:30])([CH3:29])[C@@H:18]([OH:28])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)([CH3:4])[CH3:3].C(=O)([O-])O.[Na+].[CH:39]([O:41][CH2:42][CH3:43])=[CH2:40]>ClCCl>[CH3:4][C:2]([Si:5]([CH3:32])([CH3:33])[O:6][CH2:7][C@@H:8]([CH3:31])[C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([C:17]([CH3:30])([CH3:29])[C@@H:18]([O:28][CH:39]([O:41][CH2:42][CH3:43])[CH3:40])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 8023Ethyl vinyl etherHCID 516892Sodium BicarbonateHCID 69284672HCID 69284672, compound

Product 1

HCID 69282804HCID 69282804, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

—Pyridinium p-toluenesulfonate (0.31 g) was added to a solution of (3β,20S)-21-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4,4,20-trimethylpregn-5-en-3-ol (WO9852965; 7.28 g) in dichloromethane (50 ml) and ethyl vinyl ether (20 ml). After stirring of the reaction mixture for 6 h at room temperature it was poured into a saturated aqueous solution of sodium hydrogencarbonate. The product was extracted into dichloromethane; the combined organic phases were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to give (3β,20S)-21-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(1-ethoxyethyl)oxy]-4,4,20-trimethylpregn-5-ene (8.19 g), which was used in the following step without further purification.

Workup

  1. extractionThe product was extracted into dichloromethane
  2. washthe combined organic phases were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e50ce155f7de4df48ef0df0ab6444fd7
Source dataset
uspto-grants-2003_04
Patent number
US06552011B1

Reaction notes

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