Diisopropylamine → HCID 15550613, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (3-hydroxymethyl-2-methylphenoxy)acetic acid te/t-butyl ester (80.1 g, 318 mmol) dissolved in tetrahydrofuran (400 mL) was cooled to −50° C. and treated with lithium diisopropylamide (325 mmol) freshly prepared from diisopropylamine (49 mL) and 2.5M n-butyllithium (130 mL) in tetrahydrofuran (100 mL). After about 10 minutes at −50° C., a solution of diphenylcarbamyl chloride (80.8 g, 350 mmol) dissolved in tetrahydrofuran (100 mL) was added. The entire reaction mixture was stirred for an additional 30 minutes and then allowed to warm to room temperature over a period of 3 hours. The solution was evaporated in vacuo, poured into dilute hydrochloric acid, and extracted with diethyl ether. The organic layer was dried over brine, evaporated, and purified by silica gel chromatography, eluting with acetone/hexane (1:5→1:3), to give {3-[(diphenylcarbamoyloxy)-methyl]-2-methylphenoxy}acetic acid tert-butyl ester as a white solid (104.1 g, 73%).

Provenance & Evidence