3-Chloro-1,2-propanediol → HCID 178521461, compound

Participants

Reaction Steps

1-Benzylimidazole (3.95 g, 25.0 mmol) and 3-chloro-1,2-propanediol (2.76 g, 25.0 mmol) were stirred in a 130° C. oil bath for 48 h, after which the flask was placed under vacuum and stirring continued at 130° C. for another 48 h. The residue was then dissolved in CH3OH and transferred to a tared flask and concentrated to afford the product as a viscous brown oil (6.50 g, 97%). 1H NMR: δH ppm (400 MHz; DMSO-d6) 3.18-3.30 (m, 1H) 3.37-3.49 (m, 1H) 3.73-3.86 (m, 1H) 4.15 (dd, J=13.74, 7.69 Hz, 1H) 4.36 (dd, J=13.74, 3.11 Hz, 1H) 5.21 (t, J=5.50 Hz, 1H) 5.49 (s, 2H) 5.62 (d, J=5.50 Hz, 1H) 7.32-7.50 (m, 5H) 7.80 (t, J=1.83 Hz, 1H) 7.86 (t, J=1.83 Hz, 1H) 9.49 (t, J=1.56 Hz, 1H).

Provenance & Evidence