1-Cyanocyclopropanecarboxylic acid ethyl ester
To a stirred solution of ethyl cyanoacetate (3 g, 26.53 mmol) in ethanol (30 mL), was added
sodium ethoxide (4.51 g, 66.33 mmol) portionwise at 20 °C over 0.5 h followed by 1,2-
dibromoethane (7.47 g, 39.8 mmol). The reaction mixture then was heated and stirred at
reflux for 3.5 h. After concentration under vacuum, the residue was diluted with ethyl
acetate (30 mL) and neutralized with aq. HCl (10 mL). The organic layer was separated and
the aqueous layer extracted with ethyl acetate (2 × 15 mL). The combined organic extracts
were dried over anhydrous Na2SO4 and concentrated at 40 °C under vacuum. The product
was purified by column chromatography using hexane - EtOAc as eluent to yield the title compound as a colorless liquid (2.58 g, yield 70%);
REACTANTS
ETHYL CYANOACETATE
1,2 DIBROMOETHANE
.......................................................................
1-Cyanocyclopropanecarboxylic acid ethyl ester
1H NMR (CDCl3, 300 MHz):
δ 1.34 (t,
J = 7.1 Hz, 3H,
CH3CH2O-), METHYL OF ETHYL ESTER
1.62 (t, J = 3.8 Hz, 2H,
CH2 c-propyl), CYCLOPROPYL
1.67 (t, J = 3.8 Hz, 2H,
CH2 c-propyl), CYCLOPROPYL
4.25 (q, J = 7.1 Hz, 2H, CH3
CH2O-); CH2 OF ETHYLESTER
MS (CI): 162 (M+Na, 100%);
IR (neat,
cm−1
): 2986,
2249,
NITRILE,
1736,
ESTER,
1371, 1311, 1162, 1024, 971, 858, 747;
Elemental Analysis found:
C, 60.30; H, 6.39; N, 10.24 C7H9NO2 Requires C, 60.42; H, 6.52; N, 10.07.
13 C NMR PREDICTIONS
COSY
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