Triethylamine → HCID 23001307, compound

Participants

Reaction Steps

To a solution of oxalyl chloride (3.24 mL, 6.472 mmol) in methylene chloride (10 mL) at −78° C. was added DMSO (0.919 mL, 12.9 mmol). The solution was stirred for 15 minutes and a solution of the alcohol from Step I (1.11 g, 4.32 mmol) in methylene chloride (5 mL)/DMSO (1 mL) was added. The solution was stirred for an additional 15 minutes and then triethylamine (3.01 mL, 21.6 mmol) was added. The resulting solution was stirred for 5 minutes at −78° C. and 4 hours at 25° C. The reaction was poured onto sat. aq. NaHCO3 and extracted with methylene chloride (3×20 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo to provide the title product as a brown oil which was sufficiently pure for use in the next step.

Provenance & Evidence