Methanesulfonyl chloride → HCID 54528871, compound

HRID 1197058Notes

Reaction equation

HRID 1197058 reaction equation
[Si:1]([O:8][CH:9]([CH2:38][CH2:39][CH2:40][O:41][Si:42]([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:44])[CH3:43])[CH:10]=[CH:11][CH:12]([CH:14]1[C:18](=[O:19])[C:17]([S:20][CH3:21])=[CH:16][C:15]1([CH2:27][CH2:28][CH2:29][CH2:30][O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[O:22][Si:23]([CH3:26])([CH3:25])[CH3:24])O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CS(Cl)(=O)=O.S([O-])(O)(=O)=O.[K+]>ClCCl>[Si:1]([O:8][CH:9]([CH2:38][CH2:39][CH2:40][O:41][Si:42]([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:43])[CH3:44])[CH:10]=[CH:11][CH:12]=[C:14]1[C:18](=[O:19])[C:17]([S:20][CH3:21])=[CH:16][C:15]1([CH2:27][CH2:28][CH2:29][CH2:30][O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[O:22][Si:23]([CH3:24])([CH3:25])[CH3:26])([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516920Potassium bisulfateHCID 53927203HCID 53927203, compound

Product 1

HCID 54528871HCID 54528871, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.00 g of 5-[4,7-bis(t-butyldimethylsilyloxy)-1-hydroxy-2-heptenyl]-2-methylthio-4-(4-phenoxybutyl)-4-trimethylsilyloxy-2-cyclopentenone obtained in Example 62 dissolved in 10 ml of dichloromethane was added under ice-cooling and stirring 497 mg of dimethylaminopyridene, and then 147 μl of methanesulfonyl chloride was added dropwise. The temperature of the mixture was gradually elevated to room temperature, and then stirred for 6 hours. Saturated aqueous potassium hydrogensulfate was added, and the mixture was extracted with ethyl acetate. The organic layers were combined, washed with saturated aqueous sodium hydrogencarbonate and with saturated aqueous sodium chloride in the order mentioned, and dried over anhydrous sodium sulfate. After filtration and concentration, the concentrate was subjected to silica gel chromatography to give 644 mg (yield 66%) of low polarity isomer and 255 mg (yield 26%) of high polarity isomer of 5-[4,7-bis(t-butyldimethylsilyloxy)-2-heptenylidene]-2-methylthio-4-(4-phenoxybutyl)-4-trimethylsilyloxy-2-cyclopentenone.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. customwas gradually elevated to room temperature
  4. stirringstirred for 6 hours
  5. extractionthe mixture was extracted with ethyl acetate
  6. washwashed with saturated aqueous sodium hydrogencarbonate and with saturated aqueous sodium chloride in the order
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-1eecd027056b4f3fae6207c34802953f
Source dataset
uspto-grants-1992_05
Patent number
US05116869

Reaction notes

Loading…