Réaction #78871

Équation de réaction

(±)-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

Rendement 93.6%

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   Autreat room temperature the solvent was removed in vacuum
2. 2
   Extractionthe residue was extracted with diethyl ether
3. 3
   LavageThe extract was washed with hydrochloric acid, water
4. 4
   Séchagedried over anhydrous sodium sulphate

Mode opératoire

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.

Source