(S)-3-cyclohexyl-3-hydroxypropyl 4-bromobenzenesulfonate → 3-Cyclohexyl-3-oxopropyl 4-bromobenzenesulfonate

HRID 1826476Notes

Reaction equation

HRID 1826476 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH2:13][C@@H:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[OH:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][CH2:13][C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10643291(S)-3-cyclohexyl-3-hydroxypropyl 4-bromobenzenesulfonateHCID 178418287HCID 178418287, compound

Product 1

HCID 207024703-Cyclohexyl-3-oxopropyl 4-bromobenzenesulfonateYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-3-cyclohexyl-3-hydroxypropyl 4-bromobenzenesulfonate (J. A. Werner et al, J. Org. Chem., 1996, 61, 587), (40 mg, 0.106 mmol) in dichloromethane (3 ml) was added silica (50 mg) and pyridinium chlorochromate (20 mg, 0.09 mmol), and the reaction mixture was left to stir at room temperature for 16 h. The reaction mixture was subjected to direct silica (5 g) column chromatography eluting with dichloromethane:hexane (4:1) to afford the title compound as a yellow solid (38 mg, 96%).

Workup

  1. waitthe reaction mixture was left
  2. washeluting with dichloromethane:hexane (4:1)

Sources & evidence

ORD record
ord-1bc3bea8d876499e9d6470f903828612
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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