Sodium hydride → HCID 59428169, compound

HRID 2425753Notes

Reaction equation

HRID 2425753 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[Si:9]([O:26][CH:27]1[CH2:32][CH2:31][C:30](=[O:33])[CH2:29][CH2:28]1)([C:22]([CH3:25])([CH3:24])[CH3:23])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CS(C)=O.O>[C:22]([Si:9]([O:26][CH:27]1[CH2:32][CH2:31][C:30]2([O:33][CH2:4]2)[CH2:29][CH2:28]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)([CH3:25])([CH3:23])[CH3:24]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 114168864-{[tert-Butyl(diphenyl)silyl]oxy}cyclohexan-1-one

Product 1

HCID 59428169HCID 59428169, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

To a stirred suspension of sodium hydride (60% in mineral oil, 441 mg, 11.0 mmol) in dimethylsulfoxide (7 mL) was added trimethylsulfoxonium iodide (2.53 g, 11.5 mmol) at room temperature, and the mixture was stirred at room temperature for 30 min. To this mixture was added a solution of 4-{[tert-butyl(diphenyl)silyl]oxy}cyclohexanone (3.53 g, 10.0 mmol, Okamura, William H. et al., J. Org. Chem., 1993, 58, 600) in dimethylsulfoxide (35 mL) dropwise at room temperature, and the mixture was stirred at room temperature for 2 h. Then the mixture was diluted with water (600 mL), and extracted with diethyl ether (200 mL×4). The combined organic layer was dried over magnesium sulfate, and concentrated in vacuo. The residue was chromatographed on a column of silica gel eluting with ethyl acetate/n-hexane (1:10), and then purified with plate TLC eluting with ethyl acetate/n-hexane (1:15) to give 459 mg (13%, trans) and 390 mg (11%, cis) of the title compound as a colorless oil respectively.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 h
  2. extractionextracted with diethyl ether (200 mL×4)
  3. dry with materialThe combined organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on a column of silica gel eluting with ethyl acetate/n-hexane (1:10)
  6. custompurified with plate TLC
  7. washeluting with ethyl acetate/n-hexane (1:15)

Sources & evidence

ORD record
ord-75010ff6614f494a8d8a00f910298da5
Source dataset
uspto-grants-2011_06
Patent number
US07964727B2

Reaction notes

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