반응 #42496

반응 방정식

methyl 4-butyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

9-BBN

ethanolamine

→

title compound

수율 80.1%

Methyl 4-butyl-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

수율 80.1%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   농축the resulting solution was concentrated under reduced pressure
2. 2
   세척The residue was washed with hexanes
3. 3
   여과filtered
4. 4
   농축the filtrate was concentrated under reduced pressure
5. 5
   기타Purification by flash column chromatography (silica, 25% ethyl acetate/hexanes)

실험 절차

A solution of methyl 4-butyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate (800 mg) and 9-BBN (1.6 g) in tetrahydrofuran (13 mL) was refluxed for 1.5 h. The mixture was cooled to room temperature, ethanolamine (0.4 mL) was added, and the resulting solution was concentrated under reduced pressure. The residue was washed with hexanes, filtered, and the filtrate was concentrated under reduced pressure. Purification by flash column chromatography (silica, 25% ethyl acetate/hexanes) afforded 607 mg of the title compound: 1H NMR (300 MHz, DMSO-d6) δ 7.21, 7.16, 6.75, 4.24-4.21, 3.78, 3.34-3.24, 1.55-1.47, 1.38-1.30, 0.95-0.90.

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