Reaction #1294

Reaction equation

(S)-2-phthalimido-6-hydroxyhexanoic acid

cesium carbonate

methyl iodide

→

title product

Yield 196.0%

(S)-2-Phthalimido-6-hydroxyhexanoic acid, methyl ester

Yield 196.0%

Solvents

dimethylformamide

ethyl acetate

Conditions

Workup

1. 1
   Washwashed successively with water containing a small amount of sodium bisulfite, water, 50% saturated sodium bicarbonate, and brine
2. 2
   Dryingdried (sodium sulfate)
3. 3
   Filtrationfiltered

Procedure

A slurry of (S)-2-phthalimido-6-hydroxyhexanoic acid (3.752 g., 13.5 mmol.) and cesium carbonate (2.178 g., 6.7 mmol.) in dimethylformamide (44 ml.) was treated with methyl iodide (3.0 ml., 6.84 g., 48.2 mmol.). After stirring at room temperature for 2 hours, the mixture was diluted with ethyl acetate and washed successively with water containing a small amount of sodium bisulfite, water, 50% saturated sodium bicarbonate, and brine, then dried (sodium sulfate), filtered and stripped to give the title product as a colorless oil (3.825 g.). The oil was homogeneous by TLC (1:1-acetone:hexanes) Rf =0.37.

Source