Réaction #8283

Équation de réaction

4,5-dihydroxy-pentanoic acid ethyl ester

tert-butyl-dimethyl-silyl chloride

triethylamine

→

title compound

5-(tert-Butyl-dimethyl-silyloxy)-4-hydroxy-pentanoic acid ethyl ester

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   Lavagewashed with water (100 mL), saturated ammonium chloride solution, and brine
2. 2
   FiltrationThe solution is filtered
3. 3
   Concentrationconcentrated in vacuo

Mode opératoire

A solution of 4,5-dihydroxy-pentanoic acid ethyl ester, (7 g, 43.2 mmol) and 4-dimethylaminopyridine (0.2 g, 1.73 mmol) in dichloromethane (145 mL) at room temperature under nitrogen is treated with tert-butyl-dimethyl-silyl chloride (7.8 g, 51.85 mmol) and triethylamine (6.9 mL, 47.52 mmol) and stirred 18 h. The mixture is diluted with dichloromethane (100 mL), washed with water (100 mL), saturated ammonium chloride solution, and brine. The solution is filtered and concentrated in vacuo to yield the title compound, 11.85 g (99%), as a colorless oil.

Source