反応 #1869220

反応方程式

Water

(2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate

methyl (2,4-dichloro-5-hydroxyphenoxy)acetate

Cs2CO3

→

(2,4-dichloro-5-oxiranylmethoxy-phenoxy)-acetic acid methyl ester

収率 46.4%

溶媒

DMF

反応条件

実験手順

A mixture of (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (0.4 g), methyl (2,4-dichloro-5-hydroxyphenoxy)acetate (0.39 g) and Cs2CO3 (0.58 g) in DMF (2 ml) was stirred at r.t. overnight. Water was added and (2,4-dichloro-5-oxiranylmethoxy-phenoxy)-acetic acid methyl ester (0.22 g) was isolated by filtration and dried in vacuo. 5-Chloro-3H-spiro[1-benzofuran-2,4′-piperidine] (0.16 g) in ethanol (5 ml) was added and heated at 70° C. for 2 h. The mixture was allowed to cool and water (1 ml) followed by LiOH (2 eq) was added. Stirred for 3 h. RPHPLC (Xterra, gradient 95-5%, ammonia (0.2% aq.): acetonitrile) gave the title compound (0.1 g) as a white solid.

出典