Reaktion #47091

Reaktionsgleichung

cyclooctanol

ethyl diazoacetate

→

product 413

Ausbeute 37.8%

Cyclooctyloxyacetic acid ethyl ester

Ausbeute 37.8%

Lösungsmittel

Et2O

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered through Celite
2. 2
   Sonstigethe filtrate is evaporated
3. 3
   workup.DISTILLATIONdistilled at 150° C.

Vorschrift

To a solution of cyclooctanol (640 mg, 4.9 mmol) in dichloromethane (15 mL) is added rhodium (II) acetate dimer (21 mg) followed by ethyl diazoacetate (0.60 g, 5.7 mmol). The reaction mixture is stirred at RT for 10 min. The reaction mixture is rotary evaporated, and the residue dissolved in Et2O, filtered through Celite, and the filtrate is evaporated and the residue is vacuum distilled at 150° C. to give 397 mg of the product 413. 1H NMR (CDCl3) δ 4.21 (q, 2H), 4.06 (s, 2H), 3.50 (m, 1H), 1.93 (m, 2H), 1.7-1.4 (m, 8H), 1.4-1.3 (m, 2H), 1.28 (t, 3H); MS: m/z 215 (M++1).

Quelle