Reaction #47091

Reaction equation

cyclooctanol

ethyl diazoacetate

→

product 413

Yield 37.8%

Cyclooctyloxyacetic acid ethyl ester

Yield 37.8%

Solvents

Et2O

dichloromethane

Conditions

Workup

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

Procedure

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).

Source