Reaction #56499

Reaction equation

diazomethane

4-{3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoic acid

Acetic acid

→

title compound

Methyl 4-{3-[3-[2-(1-Hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoate

Solvents

ether

ether

Conditions

Workup

1. 1
   Otherto destroy the excess diazomethane
2. 2
   Washthe solution is washed with dilute sodium bicarbonate solution
3. 3
   Dryingdried over sodium sulfate
4. 4
   OtherEvaporation of volatile materials in vacuo

Procedure

A solution of diazomethane (approximately 2.5 g., 0.06 mole) in ether (100 ml.) is mixed with a solution of 4-{3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoic acid (11.7 g., 0.03 mole) in ether (100 ml.). The resulting solution is allowed to stand at room temperature for 6 hours. Acetic acid is then added to destroy the excess diazomethane, and the solution is washed with dilute sodium bicarbonate solution and dried over sodium sulfate. Evaporation of volatile materials in vacuo yields the title compound as a nearly colorless, viscous oil.

Source