Triethylamine → HCID 20534691, compound

Participants

Reaction Conditions

Reaction Steps

The alcohol/propionate mixture was dissolved in MTBE (100 ml) , and the solution was cooled to 5° C. Triethylamine (10.8 ml, 78 mmol) was added. The solution was cooled to 0-2° C. and methanesulfonyl chloride (3.75 ml, 48.5 mmol) was added over 30 minutes, maintaining the internal temperature at 0-2° C. The suspension was stirred at 0-2° C. for 15 minutes, and extra methanesulfonyl chloride (0.2 ml, 2.6 mmol) was then added. The suspension was stirred at 0-2° C. for 5 minutes, and then the reaction was quenched with water (85 ml). The aqueous layer was removed, and the organic layer was washed with saturated potassium hydrogen sulfate solution-water (1:1, 80 ml), saturated sodium bicarbonate solution (80 ml) and brine (40 ml). After drying (MgSO4), filtration and evaporation of the solvent, the mesylate/propionate mixture was obtained as a yellow oil (26 g). 1H nmr (200 MHz, CDCl3) δ ppm 7.27-6.92 (2 H total, m), 6.84-6.78 (1 H total, m) 5.74 (1 H propionate, td, J5.8, 2.3 Hz), 5.51 (1 H mesylate, td, J5.6, 2.4 Hz), 4.25 (2 H, mesylate, d, J 4.9, 4.19 (1 H propionate, d, J5.5 Hz), 3.16 (3 H mesylate, s), 2.79 (1 H mesylate, J2.4 Hz), 2.53 (1 H propionate, J2.1 Hz), 2.39 (2 H propionate, q, J7.6 Hz) and 1.16 (3 H propionate, t, J7.5 Hz)

Provenance & Evidence