Sodium hydride → 3-(2-Chloro-phenylsulfanyl)-cyclopentanecarboxylic acid methyl ester

反応式

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[H-].[Na+].[CH3:11][O:12][C:13]([CH:15]1[CH2:19][CH2:18][CH:17](OS(C)(=O)=O)[CH2:16]1)=[O:14]>C1COCC1>[CH3:11][O:12][C:13]([CH:15]1[CH2:19][CH2:18][CH:17]([S:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[CH2:16]1)=[O:14]

参加物

実験手順

A solution of 2-chlorothiophenol (0.19 g, 1.5 eq) in THF (6.0 mL) was treated with NaH (60% dispersion in mineral oil, 0.05 g, 1.5 eq). The resulting solution was stirred at RT for 30 min. A solution of 3-methanesulfonyloxy-cyclopentanecarboxylic acid methyl ester (0.20 g, 1.0 eq) in THF (2.0 mL) was then added dropwise. The mixture was warmed at 50° C. and stirred for 3 h. The mixture was partitioned between 1N sodium bicarbonate and ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated. The title compound was obtained as a colorless oil (0.24 g, 98%) and was used without further purification in the next step. MS (ESI): m/z=271.2 [M+H]+.