Propionic Acid → O-Propanoyloxymethyl S-Ethyl Carbonothioate

Participants

Reaction Steps

To a stirred solution of NaHCO3 (45 g, 536 mmol) in H2O (540 ml) is added TBA HSO4 (91.2 g, 268 mmol), propanoic acid (20.1 mL, 268 mmol), and CH2Cl2 (540 ml). Following stirring for 1 h at room temperature a solution of 5b (49.2 g, 200 mmol) in CH2Cl2 (100 mL) is added during 45 min keeping the temperature below 30° C. The stirring is continued for 11/2 h. The organic phase is separated, washed with H2O (200 mL), dried (MgSO4), and evaporated. The residue is stirred in Et2O (800 mL) during the night, filtered, and washed with Et2O (50 mL). The filtrate is evaporated and distilled to yield 38.0 g (98%) of 6cb, bp 71°-73° C./0.3 mbar.

Provenance & Evidence