Reaction #47102

Reaction equation

1-cyclopentylethan-1-ol

ethyl diazoacetate

→

product 452

Yield 44.8%

(1-Cyclopentylethoxy)acetic acid ethyl ester

Yield 44.8%

Solvents

heptane

dichloromethane

Conditions

Workup

1. 1
   Filtrationfiltered
2. 2
   OtherThe filtrate is evaporated
3. 3
   Otherthe residue is purified by chromatography on silica gel
4. 4
   Washelution with EtOAc:heptane (1:9)

Procedure

To a solution of 1-cyclopentylethan-1-ol (1.14 g, 10.0 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (10 mg) followed by ethyl diazoacetate (0.95 mL, 9.03 mmol). The reaction mixture is stirred at rt for 0.5 h. The reaction mixture is diluted with heptane, and filtered. The filtrate is evaporated, and the residue is purified by chromatography on silica gel; elution with EtOAc:heptane (1:9) gives 0.81 g of the product 452. 1H NMR (CDCl3) δ 4.30-4.15 (m, 2 H), 4.09 (d, 2 H), 3.25-3.15 (m, 1 H), 2.00-1.78 (m, 2 H), 1.75-1.35 (m, 6 H), 1.29 (t, 3 H), 1.15 (d, 3 H).

Source