Reaction #983944

Reaction equation

sodium

4-hydroxybutyric acid

4-nitrophenol

N,N′-dicyclohexylcarbodiimide

4,4′-dimethoxytrityl chloride

→

desired compound

4-Nitrophenyl 4-(4,4′-dimethoxytrityloxy)butyrate

Solvents

pyridine

Conditions

Workup

1. 1
   FiltrationThe precipitated dicyclohexylurea is filtered off
2. 2
   Washwashed with dichloromethane
3. 3
   ConcentrationThe filtrate is concentrated
4. 4
   OtherThe residue is purified on a silica gel column (10-50% ethyl acetate and 1% triethylamine in petroleum ether)

Procedure

The sodium salt of 4-hydroxybutyric acid (1.26 g; 10 mmol) is dissolved in anhydrous pyridine (30 ml), and 4,4′-dimethoxytrityl chloride (3.39 g; 3.05 mmol) is added. After 16 hours, 4-nitrophenol (1.39 g; 10 mmol) and N,N′-dicyclohexylcarbodiimide (2.06 g; 10 mmol) are added, and the mixture is stirred at 22° C. for a further 48 hours. The precipitated dicyclohexylurea is filtered off and washed with dichloromethane. The filtrate is concentrated and the resulting residue is coevaporated twice with toluene. The residue is purified on a silica gel column (10-50% ethyl acetate and 1% triethylamine in petroleum ether). The desired compound is obtained in the form of a pale yellowish-colored oil.

Source