Pyridine → HCID 71582576, compound

Participants

Reaction Conditions

Reaction Steps

To this solution, DMAc (200 mL), pyridine (145 g, 2.5 eq.), DMAP (8.97 g, 0.10 eq.), and succinic anhydride (73.5 g, 1.0 eq.) were added in this order, and the mixture was stirred at 60° C. for 8 hours. The reaction mixture was cooled to room temperature and then washed with water (600 mL) to obtain an organic layer. The aqueous layer was subjected to extraction twice with TBME (200 mL for each). The combined organic layers were washed with 2 M hydrochloric acid (1.0 L), then further washed twice with a 5% aqueous sodium bicarbonate solution (1.0 L for each), and concentrated. The concentrated residue was diluted with hexane (500 mL), washed with a 5% aqueous sodium bicarbonate solution (500 mL) and 20% saline (200 mL) in this order, and then concentrated. The residue was distilled (pressure: 2.8 to 3.0 kPa, distillation temperature: 102 to 104° C.) to obtain (1R,5S)-3-ethylbicyclo[3.2.0]hept-3-en-6-one (41.3 g, yield: 41%, 97.7% ee).

Provenance & Evidence