Reaktion #47108

Reaktionsgleichung

cyclopropyl-1-ethanol

ethyl diazoacetate

→

product 471

Ausbeute 71.6%

(1-Cyclopropyl-1-ethoxy)acetic acid ethyl ester

Ausbeute 71.6%

Lösungsmittel

heptane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered through Celite
2. 2
   Sonstigethe filtrate is evaporated
3. 3
   workup.DISTILLATIONdistilled at 130° C.

Vorschrift

To a solution of cyclopropyl-1-ethanol (860 mg, 10.0 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (10 mg) followed by ethyl diazoacetate (0.95 mL, 9.0 mmol). The reaction mixture is stirred at rt for 30 min. The reaction mixture is diluted with heptane, filtered through Celite, and the filtrate is evaporated and the residue is vacuum distilled at 130° C. to give 1.11 g of the product 471. 1H NMR (CDCl3) δ 4.12 (s, 2H), 4.10 (q, 2H), 2.86 (m, 1H), 1.25-1.15 (m, 6H), 0.8-0.7 (m, 1H), 0.55-0.3 (m, 3H), 0.05-0.02 (m, 1H); MS: m/z 173 (M++1).

Quelle