Chloroacetaldehyde → HCID 55298321, compound

Participants

Reaction Steps

To a solution of 3-fluoropyrrolidine hydrochloride (0.59 g, 4.7 mmol) in 1,2-dichloroethane (8.2 mL) and AcOH (0.54 mL) was added chloroacetaldehyde (0.74 mL, 4.7 mmol, 50% in H2O solution) and Na(AcO)3BH (3.7 g, 17 mmol). The reaction mixture was stirred at ambient temperature for 1 h, and then the reaction mixture was diluted with 1 N NaOH and extracted with CH2Cl2 (3×50 mL). The organics were washed with brine (2×25 mL), dried (Na2SO4) and concentrated to yield the title compound (0.242 g, 33%) as a red-orange oil: 1H NMR (500 MHz, DMSO-d6) δ 5.24-5.11 (m, 1H), 4.25-4.23 (m, 1H), 3.60 (t, J=7.0 Hz, 2H), 2.95-2.82 (m, 4H), 2.60-2.56 (m, 1H), 2.20-2.04 (m, 2H); ESI MS m/z 152 [M+H]+.

Provenance & Evidence