Triethylamine → HCID 53958373, compound

Participants

Reaction Steps

Triethylamine (2.49 ml, 17.88 mmol) was added to a stirred solution of ethyl 8-dimethylamino-6,6-diphenyl-5-hydroxynon-2-enoate (1.77 g, 4.47 mmol) in CH2Cl2 (30 ml) at -30° C. (CCl4 /acetone/CO2), and the solution was stirred for 5 min. Trifluoromethanesulfonyl chloride (0.38 ml, 4.91 mmol) was then added dropwise. The reaction mixture was stirred 15 min at -30° C., warmed to room temperature over 1 hour, and then stirred at room temperature for 2 hours. The mixture was diluted with CH2Cl2 (20 ml) and poured into 5% NaHCO3 (20 ml). The layers were separated, and the organic extracts were washed with brine (30 ml). The extracts were dried over Na2SO4 /trace K2CO3, filtered, and concentrated in vacuo on a rotary evaporator. The oily brown residue was applied to a column as described above, and eluted with 6% methanol in CHCl3 to yield 1.05 g of ethyl 6,6-diphenyl-8-dimethylaminonona-2,4-dienoate, as a clear light brown mobile oil.

Provenance & Evidence