Water → HCID 54133031, compound

HRID 399965Notes

Reaction equation

HRID 399965 reaction equation
[Si]([O:8][C@@H:9]1[C@@:28]2([CH3:29])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:30])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[C:21](=[O:23])[CH3:22])[CH2:12][C@@H:11]([O:31][Si](C(C)(C)C)(C)C)[CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[OH:8][C@@H:9]1[C@@:28]2([CH3:29])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:30])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[C:21](=[O:23])[CH3:22])[CH2:12][C@@H:11]([OH:31])[CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 53816041HCID 53816041, compound

Product 1

HCID 54133031HCID 54133031, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, to a solution of 1α,3β-bis(t-butyldimethylsilyloxy)-20-oxopregna-5,7-diene (4.10 g, 7.33 mmol) in dry tetrahydrofuran (80 ml), was added tetra-n-butylammonium fluoride (1M solution in tetrahydrofuran, 74 ml, 74.0 mmol), and the mixture was refluxed for 16 hours. Then the mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with 10% hydrochloric acid, an aqueous saturated sodium bicarbonate solution and brine, and dried over magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by column chromatography on silica gel (dichloromethane:ethanol=15:1) to give the title compound (1.68 g, 69%) as a white solid.

Workup

  1. temperaturethe mixture was refluxed for 16 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed successively with 10% hydrochloric acid
  4. dry with materialan aqueous saturated sodium bicarbonate solution and brine, and dried over magnesium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (dichloromethane:ethanol=15:1)

Sources & evidence

ORD record
ord-4760410fad2441e3b492b56a38e63788
Source dataset
uspto-grants-1998_10
Patent number
US05824811

Reaction notes

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