Reaktion #47097

Reaktionsgleichung

2-(2-chlorophenoxy)ethanol

ethyl diazoacetate

MeOH

→

product 436

Ausbeute 52.6%

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

Ausbeute 52.6%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle