Methanol → HCID 18376321, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 8.7 g (63.3 mmol) of thiobenzamide and 10 g (42.2 mmol) of ethyl 4-bromo-3-oxo-hexanoate in 45 mL of toluene was refluxed for 6 hrs with Dean-Stark trap removal of water. Cooled, added methanol, and continued reflux for 1 h. Cooled, partially concentrated (˜½ volume), then 30 mL of 2.0 M NaOH solution was added. Stirred the mixture at 80° C. for 2 hrs before cooling and extraction of the aqueous with EtOAc. The aqueous phase was treated with 70 mL of 1.0 M citric acid with heating (70° C.) for 45 min. The mixture was extracted with EtOAc, and the extracts were dried. over MgSO4, filtered and concentrated to yield a yellow colored solid upon standing at ambient temperature (8.4 g, ˜80% yield); 1H NMR (CDCl3, 300 MHz) δ7.95-7.87 (m, 2H), 7.48-7.45 (m, 3H), 3.86 (s, 2H), 2.85 (q, 2H, J=7.5), 1.36 (t, 3H, J=7.5).

Provenance & Evidence