Propargyl bromide → HCID 129865535, compound

Participants

Reaction Steps

Propargyl-choline was synthesized by the following procedure: 4 grams of propargyl bromide (80% solution in toluene, 34 mmoles) were slowly added to 3 grams of dimethyl-ethanolamine (34 mmoles) in 10 mL of dry THF, while stirring on ice. The mix was allowed to reach room temperature and stirring was continued overnight. The resulting white solid was filtered and washed extensively with cold THF (10 times, 20 mL), to afford pure propargyl-choline bromide (5.9 grams, 84% yield) as a white solid. Propargyl-choline: white crystals, molecular weight: 128.19, ES-API LC/MS: [M]+=128.1, 1H NMR (600 MHz, CD3OD): 4.78 (1H, b), 4.49 (2H, d, J=2.4 Hz), 4.03 (2H, t, J=4.5 Hz), 3.64 (2H, m), 3.30 (6H, s), 13C NMR (600 MHz, CD3OD): δ3.2 (CH, d, J=101.4 Hz), 72.7 (C, d, J=21.0 Hz), 66.4 (CH2, t, J=60.3 Hz), 56.7 (CH2, t, J=47.4 Hz), 56.5 (CH2, t, J=45.9 Hz), 52.2 (C2H6, q, J=31.2 Hz), 49.05 (CD3OD).

Provenance & Evidence