Methanesulfonyl chloride → HCID 54528871、化合物

HRID 1197058ノート

反応式

HRID 1197058 の反応式
[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]

参加物

5

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 516920Potassium bisulfateHCID 53927203HCID 53927203、化合物

生成物 1

HCID 54528871HCID 54528871、化合物収率 66%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1eecd027056b4f3fae6207c34802953f
出典データセット
uspto-grants-1992_05
特許番号
US05116869

反応ノート

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