Triethylamine → 4-Heptyl-N-hydroxy-N-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of N-methylhydroxylamine hydrochloride (701 mg, 2 eq.) in 20 ml of THF:H2O (1:1) with triethylamine (1.75 ml, 3.0 eq.) was added 4-n-heptyl benzoic acid chloride (1.0 g, 4.2 mmol). The solution was stirred for 1/2 hour at 0° C. then allowed to warm to room temperature and stir overnight. The reaction mixture was diluted with EtOAc and the organic layer washed with H2O, 1N HCl (2×), and brine, then dried over anhydrous MgSO4. Concentration in vacuo gave an oil which was flash chromatographed on LPS-1 silica gel eluting with (1:1) hexane:EtOAc. Product containing fractions were concentrated in vacuo to yield title product, 448 mg (43%) as a light yellow oil which solidified upon standing. TLC (1:1) Hexane:EtOAc Rf =0.18, UV+PMA. Product streaks to baseline.

Provenance & Evidence