Water → HCID 57209521, compound

HRID 1385627Notes

Reaction equation

HRID 1385627 reaction equation
CC([Si](C)(C)[O:6][CH2:7][C@@H:8]([CH3:36])[C@@H:9]1[C@:26]2([CH3:27])[C:12]([C:13]3[CH2:14][CH2:15][C@@H:16]4[C@:21]([C:23]=3[CH2:24][CH2:25]2)([CH3:22])[CH2:20][CH2:19][C@H:18]([O:28][CH:29]([O:31][CH2:32][CH3:33])[CH3:30])[C:17]4([CH3:35])[CH3:34])=[CH:11][CH2:10]1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[CH2:32]([O:31][CH:29]([O:28][C@H:18]1[CH2:19][CH2:20][C@@:21]2([CH3:22])[C@@H:16]([CH2:15][CH2:14][C:13]3[C:12]4[C@:26]([CH3:27])([CH2:25][CH2:24][C:23]=32)[C@@H:9]([C@H:8]([CH3:36])[CH2:7][OH:6])[CH2:10][CH:11]=4)[C:17]1([CH3:35])[CH3:34])[CH3:30])[CH3:33]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 70167473HCID 70167473, compound

Product 1

HCID 57209521HCID 57209521, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

vi)—A solution of (3β,5α,20S)-21-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(1-ethoxyethyl)oxy]-4,4,20-trimethylpregna-8,14-diene (11.6 g) in a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (43 ml) was stirred at 50° C. for 1 h. The reaction mixture was poured into water and the product was extracted into ethyl acetate. The combined organic phases were washed with a saturated aqueous solution of sodium hydrogencarbonate and brine, dried over sodium sulfate, and concentrated under reduced pressure. Column chromatography afforded (3β,5α,20S)-3-[(1 -ethoxyethyl)oxy]-4,4,20-trimethylpregna-8,14-dien-21-ol (9.11 g).

Workup

  1. extractionthe product was extracted into ethyl acetate
  2. washThe combined organic phases were washed with a saturated aqueous solution of sodium hydrogencarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-81a5bc010aad4151aed3c6423c75cbd6
Source dataset
uspto-grants-2001_07
Patent number
US06262282B1

Reaction notes

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