반응 #515005

반응 방정식

ethyl acetate

tert-butyl-4-hydroxy phenyl acetate

t-butyl-4-hydroxy-phenyl acetate

2,2,4,4-tetramethyl chroman-6-carboxylic acid

Reagent E

4-Hydroxy phenyl acetic acid-t-butyl ester

→

title compound

수율 55.0%

2,2,4,4-Tetramethyl-chroman-6-carboxylic acid 4-(tert-butoxycarbonylmethyl)phenyl ester

수율 55.0%

용매

hexane

thionyl chloride

반응 조건

후처리

1. 1
   기타The thionyl chloride was evaporated under reduced pressure
2. 2
   workup.DISSOLUTIONthe residue was dissolved in 5 mL of dichloromethane
3. 3
   workup.ADDITIONtreated with triethyl amine (5 mL)

실험 절차

A solution of 2,2,4,4-tetramethyl chroman-6-carboxylic acid (0.1 g, 0.43 mmol) in thionyl chloride (10 mL) was refluxed for 2 h. The thionyl chloride was evaporated under reduced pressure and the residue was dissolved in 5 mL of dichloromethane and treated with triethyl amine (5 mL) followed by tert-butyl-4-hydroxy phenyl acetate (Reagent E, 0.088 g, 0.427 mmol). After 0.5 h, the reaction mixture was subjected to flash column chromatography over silica gel (230-400 mesh) using 5-10% ethyl acetate in hexane as the eluent to afford the title compound (0.1 g, 55%).

출처