Hydrochloric Acid → Methyl 1-(hydroxymethyl)cyclopropane-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of cyclopropane-1,1-dicarboxylic acid methyl ester (9 g, 62.4 mmol) in THF (180 mL), is cooled to 0° C. and triethylamine (9.7 mL, 69.6 mmol) and 3-methyl-butyryl chloride (9.1 mL, 9.6 mmol) are added and the reaction stirred for 1 h. In a separate flask, sodium borohydride (7.1 g, 188 mmol) is dissolved in THF (100 mL)/H2O (25 mL) and cooled to 0° C. The mixed anhydride is filtered through a sintered funnel to remove salts from previous reaction and added to the flask containing sodium borohydride and the reaction stirred for 1 h at 0° C. 1 N HCl is added and the product is extracted with EtOAc and then with CCl3H/iPrOH. It is then purified via FCC eluting with Heptane/EtOAc (100:0 to 20:80) to give 1-hydroxymethyl-cyclopropanecarboxylic acid methyl ester. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.61 (t, J=5.81 Hz, 1 H)3.59 (s, 3 H)3.55 (d, J=6.06 Hz, 2 H)1.01 (d, J=3.03 Hz, 2 H)1.01 (d, J=10.36 Hz, 1 H)0.87 (d, J=3.03 Hz, 1 H)0.85-0.88 (m, 1 H).

Provenance & Evidence