Diethyl Ether → HCID 57447690, compound

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Reaction Conditions

Reaction Steps

2-Methoxy-N-methylethanamine 266 (10.0 g, 112 mmol) was added dropwise to a stirred aqueous solution of glycolonitrile (55%, 12.0 mL, 123 mmol) at 0° C. and the mixture stirred at 70° C. for 1 h. The solution was cooled to 20° C., and Et2O (150 mL) and water (100 mL) were added. The aqueous layer was extracted with Et2O (3×40 mL), the combined organic fraction dried and the solvent evaporated to give nitrile 267 (6.46 g, 45%) as a colourless oil: 1H NMR [(CD3)2SO] δ 3.63 (s, 2H, CH2CN), 3.50 (t, J=5.1 Hz, 2H, CH2O), 3.37 (s, 3H, OCH3), 2.69 (t, J=5.1 Hz, 2H, CH2N), 2.42 (s, 3H, NCH3); HRMS calcd for C6H12N2O (M+) m/z 128.0947, found 128.0946.

Provenance & Evidence