Reaction #47097

Reaction equation

2-(2-chlorophenoxy)ethanol

ethyl diazoacetate

MeOH

→

product 436

Yield 52.6%

2-[2-(2-Chlorophenoxy)ethoxy]acetic acid ethyl ester

Yield 52.6%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Otherthe residue is purified by chromatography on silica gel
2. 2
   Washelution with EtOAc:heptane (25:75)

Procedure

To a solution of 2-(2-chlorophenoxy)ethanol (1.73 mL, 10.0 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (11 mg) followed by ethyl diazoacetate (1.05 mL, 10.0 mmol). The reaction mixture is stirred at rt for 20 min. To the reaction mixture is added MeOH followed by rotary evaporated, and the residue is purified by chromatography on silica gel; elution with EtOAc:heptane (25:75) gives 1.36 g of the product 436. 1H NMR (CDCl3) δ 7.35 (d, 1 H), 7.19 (d, 1 H), 6.95-6.90 (m, 2 H), 4.30 (s, 2 H), 4.25-4.15 (m, 4 H), 4.0 (t, 2 H), 1.2 (t, 3 H); MS: m/z 259 (M++1).

Source