反応 #464487

反応方程式

1,2-epoxycyclopentane

3-methoxyphenylmagnesium bromide

ethyl acetate

hydrochloric acid

→

1-hydroxy-2-(3-methoxyphenyl)-cyclopentane

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   洗浄the organic layer was washed with saturated sodium bicarbonate aqueous solution and brine
2. 2
   濃縮The combined organic extracts were concentrated
3. 3
   その他the residue was purified by column chromatography on silica gel

実験手順

To a solution of a mixture of 1,2-epoxycyclopentane (7.0 g) and copper(I) chloride (260 mg) in tetrahydrofuran (70 ml) was added 3-methoxyphenylmagnesium bromide (53.5 m mol) in tetrahydrofuran (60 ml) at -78° C. under N2. The mixture was stirred for 1 hour at 0° C. The reaction mixture was poured into a mixture of ethyl acetate and 1N-hydrochloric acid and then the organic layer was washed with saturated sodium bicarbonate aqueous solution and brine. The combined organic extracts were concentrated and the residue was purified by column chromatography on silica gel to give 1-hydroxy-2-(3-methoxyphenyl)-cyclopentane (13 g).

出典