Triethylamine → Bicyclo[2.2.1]hept-5-ene-2-ethanol

Participants

Reaction Conditions

Reaction Steps

NBCH2CH2O2CCH═CHC6H4OMe (EtMeOCinnNB): A 100 mL, 3 neck RBF equipped with a thermowell, addition funnel, and mechanical stirrer was charged with NBCH2OH (2 g, 14.47 mmol), DMAP (88.4 mg, 0.72 mmol, 5 mol %), 10.1 mL triethylamine (72.4 mmol) and 25 mL dichloromethane. The mixture was stirred at room temperature for 45 minutes before the addition of 4-methoxycinnamoyl chloride (3.1 g, 15.9 mmol) in 5 mL dichloromethane from the addition funnel was started. After this addition was completed, the mixture was stirred at 25° C. overnight. After confirmation of complete reaction by GC the reaction mixture was diluted with 20 mL dichloromethane, followed by washes with (2×25 mL) NaHCO3 solution, (2×15 mL) NH4Cl solution, (2×25 mL) brine, dried over Na2SO4 and filtered. Concentration of the filtrate gave 3.9 g of crude product as a colorless, viscous oil (93% crude yield) with 96% crude purity by GC.

Provenance & Evidence