Phenol → trans-3-Hydroxy-4-phenoxy-1-(beta,beta,beta-trichloroethoxycarbonyl)-pyrrolidine

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Reaction Steps

2.6 g (0.01 mol) of the 3,4-epoxy-1-(β,β,β-trichloroethoxycarbonyl)-pyrrolidine described in Example 1 are heated together with 1.88 g (0.02 mol) of phenol and 10 ml of 1 N sodium hydroxide solution in 30 ml of acetonitrile for 5 hours under reflux. After cooling, the reaction mixture is diluted with water and extracted 3 times with methylene chloride, and the organic phase is washed twice with 2 N sodium hydroxide solution and then once with water, dried over sodium sulphate and evaporated under a water pump vacuum. The resulting oil crystallises from methylene chloride/hexane and gives trans-3-hydroxy-4-phenoxy-1-(β,β,β-trichloroethoxycarbonyl)-pyrrolidine with a melting point of 100°-103°.

Provenance & Evidence