反応 #445557

反応方程式

4(RS)-t-butyldimethylsilyloxy-2,3-epoxy cyclopentanone

5-hydroxy-1-pentanethiol

methanol

triethylamine

→

4-t-butyldimethylsilyloxy-2-(6-hydroxyhexylthio)-2-cyclopentenone

収率 31.0%

反応条件

後処理

1. 1
   その他the solvent was evaporated
2. 2
   その他to give 2.1 g of a crude product
3. 3
   その他to dry column chromatography

実験手順

1.26 g (5.94 mmoles) of 4(RS)-t-butyldimethylsilyloxy-2,3-epoxy cyclopentanone and 804 mg (6.0 mmoles) of 5-hydroxy-1-pentanethiol were dissolved in 10 ml of methanol, and 606 mg (6 mmoles) of triethylamine was added. After the reaction was carried out for 10 minutes, the solvent was evaporated to give 2.1 g of a crude product. The crude product was subjected to dry column chromatography and developed with hexane/ethyl acetate (7/3) to give 710 mg (2.16 mmoles; yield 31%) of 4-t-butyldimethylsilyloxy-2-(6-hydroxyhexylthio)-2-cyclopentenone.

出典