Reaction #632003

Reaction equation

product

2-ethylcyclopropane-1,1-dicarboxylic acid di-tert-butyl ester

potassium tert-butoxide

→

desired product

Yield 69.0%

racemic 2-Ethylcyclopropane-1,1-dicarboxylic acid tert-butyl ester

Yield 69.0%

Solvents

water

diethyl ether

H2O

Conditions

Workup

1. 1
   Washwashed with diethyl ether (3×)
2. 2
   Otherwas adjusted to acidic pH with a 10% aqueous citric acid solution at 0° C.
3. 3
   Extractionextracted with ethyl acetate (3×)
4. 4
   WashThe combined organic layers were washed with water (2×), brine
5. 5
   Dryingdried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated in vacuo

Procedure

The product of Step 1 (18.3 g, 67.8 mmol) was added to a suspension of potassium tert-butoxide (33.55 g, 299.0 mmol) in dry diethyl ether (500 mL) at 0° C., treated with H2O (1.35 mL, 75.0 mmol), and was vigorously stirred overnight at room temperature. The reaction mixture was poured in a mixture of ice and water and washed with diethyl ether (3×). The aqueous layer was adjusted to acidic pH with a 10% aqueous citric acid solution at 0° C. and extracted with ethyl acetate (3×). The combined organic layers were washed with water (2×), brine, dried (MgSO4), filtered, and concentrated in vacuo to provide the desired product as a pale yellow oil (10 g, 46.8 mmol, 69% yield).

Source