Reaction #47090

Reaction equation

cycloheptanol

ethyl diazoacetate

→

product 411

Yield 95.9%

Cycloheptyloxyacetic acid ethyl ester

Yield 95.9%

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 cycloheptanol (0.600 mL, 5.0 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 0.960 g of the product 411. 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 201 (M++1).

Source