Triethylamine → HCID 19047186, compound

Participants

Reaction Conditions

Reaction Steps

2.0 g (0.0073 mol) of the title compound of Step D was added to 50 mL of methylene chloride. 1.27 mL (0.0146 mol) of oxalyl chloride (purchased from Janssen) was added followed by 2 drops of N,N-dimethylformamide. The mixture was refluxed under nitrogen for 2 h and then was evaporated to dryness. 50 mL of methylene chloride was added to the residue and then evaporated to dryness. Another 50 mL of methylene chloride was added to the residue and the solution was cooled to about 0° C. 0.90 g (0.0080 mol) of 1,3-cyclohexanedione (purchased from Aldrich Chemical Company) was added followed by 2.8 mL (0.020 mol) of triethylamine, and the mixture was stirred overnight while warming to room temperature. The mixture was evaporated to dryness, the residue was stirred in 100 mL of water and filtered. The crude product was washed with hexane to yield 2.32 g of the title compound of Step E as a solid melting at 133°-134° C. 1H NMR (CDCl3): δ 1.48 (s,6H), 2.1 (m,2H), 2.4 (m,4H), 2.6 (m,2H), 2.7 (s,3H), 3.4 (m,2H), 6.06 (s,1H).

Provenance & Evidence