반응 #78871

반응 방정식

(±)-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropan-1-ol

pyridine

p-toluenesulphonyl chloride

→

(±)-toluene-4-sulphonic acid 3-(2-benzyloxy-5-bromophenyl)-3-phenylpropyl ester

수율 93.6%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   기타at room temperature the solvent was removed in vacuum
2. 2
   추출the residue was extracted with diethyl ether
3. 3
   세척The extract was washed with hydrochloric acid, water
4. 4
   건조dried over anhydrous sodium sulphate

실험 절차

A cooled (5° C.) solution of (±)-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropan-1-ol (108.0 g) in dichloromethane (300 ml) was treated with pyridine (79.4 ml) and then p-toluenesulphonyl chloride (60.6 g) in dichloromethane (200 ml). After 18 hrs. at room temperature the solvent was removed in vacuum and the residue was extracted with diethyl ether. The extract was washed with hydrochloric acid, water, and dried over anhydrous sodium sulphate to give (±)-toluene-4-sulphonic acid 3-(2-benzyloxy-5-bromophenyl)-3-phenylpropyl ester as a light yellow oil after concentration under reduced pressure (140.3 g, 93.6% yield), tlc: (1) 0.66. NMR (CDCl3): 21.67, 33.67, 39.69, 68.58, 70.28, 113.21, 113.76, 126.47, 127.84, 128.10, 128.25, 128.41, 128.51, 129.81, 130.26, 130.42, 132.91, 134.39, 136.41, 142.16, 155.07.

출처