Реакция #42465

Уравнение реакции

Methyl 4-butyl-8-iodo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

9-BBN

ethanolamine

→

title compound

Выход 91.5%

Methyl 4-butyl-8-iodo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

Выход 91.5%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Температураat reflux for 1.5 h
2. 2
   Концентрированиеthe resulting solution was concentrated under reduced pressure
3. 3
   ПромывкаThe residue was washed with hexanes
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеthe filtrate was concentrated under reduced pressure
6. 6
   ДругоеPurification by flash column chromatography (silica, 10% ethyl acetate/hexanes)

Методика

A solution of Methyl 4-butyl-8-iodo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate (680 mg) and 9-BBN (900 mg) in tetrahydrofuran (30 mL) was heated at reflux for 1.5 h. The mixture was cooled to room temperature, ethanolamine (0.22 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, 10% ethyl acetate/hexanes) afforded 600 mg of the title compound: 1H NMR (300 MHz, CDCl3) δ 7.75, 7.28, 4.34, 3.86, 3.36, 3.28, 1.58, 1.40, 0.96.

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