反应详情

温度

0 °C

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.

1. temperatureto warm to room temperature
2. stirringstir overnight
3. washthe organic layer washed with H2O, 1N HCl (2×), and brine
4. dry with materialdried over anhydrous MgSO4
5. concentrationConcentration in vacuo
6. customgave an oil which
7. customchromatographed on LPS-1 silica gel eluting with (1:1) hexane
8. additionProduct containing fractions
9. concentrationwere concentrated in vacuo