Reaction #47088

Reaction equation

cyclohexanol

ethyl diazoacetate

→

product 407

Cyclohexyloxyacetic acid ethyl ester

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 cyclohexanol (1.0 g, 0.95 mmol) in dichloromethane (30 mL) is added rhodium (II) acetate dimer (44 mg) followed by ethyl diazoacetate (1.14 g, 10.0 mmol). The reaction mixture is stirred at RT for 20 min. The reaction mixture is diluted with Et2O, filtered through Celite, and the filtrate is evaporated and the residue is vacuum distilled at 150° C. to give 1.57 g of the product 407. 1H NMR (CDCl3) δ 4.23 (q, 2H), 4.10 (s, 2H), 3.33 (m, 1H), 1.93 (m, 2H), 1.74 (m, 2H), 1.54 (m, 1H), 1.4-1.1 (m, 8H)

Source