تفاعل #42496

معادلة التفاعل

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

9-BBN

ethanolamine

→

title compound

المردود 80.1%

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

المردود 80.1%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   تركيزthe resulting solution was concentrated under reduced pressure
2. 2
   غسيلThe residue was washed with hexanes
3. 3
   ترشيحfiltered
4. 4
   تركيزthe filtrate was concentrated under reduced pressure
5. 5
   أخرىPurification by flash column chromatography (silica, 25% ethyl acetate/hexanes)

الإجراء التجريبي

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.

المصدر