Dimethylformamide → HCID 86674674, compound

Participants

Reaction Steps

A mixture of (R)-1-(2,3-bis(benzyloxy)propyl)cyclopropane-1-sulfonic acid (630 g) and DMF (30 mL) in SOCl2 (1.5 L) was refluxed for 2 hours until HPLC analysis showed the reaction had gone to completion. The reaction mixture was concentrated to dryness and the residue purified on silica gel chromoatography with eluent: heptane for 5 minutes, then IPAC: heptanes=1:30; heptanes 1:10 resulting in the product as a red oil (298.5 g; 52% yield; 95% purity). 1H NMR (CDCl3, 400 MHz): δ 7.34 (m, 10H), 4.68 (d, 1H), 4.56 (bs, 1H), 4.53 (d, 1H), 4.16 (m, 1H), 3.54-3.62 (m, 2H), 2.63 (dd, 1H), 2.01 (q, 1H), 1.52-1.81 (m, 3H), 1.16 (m, 1H), 2.22 (bs, 1H), 1.75 (t, 2H), 1.38-1.40 (m, 2H).

Provenance & Evidence