تفاعل #42465

معادلة التفاعل

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

9-BBN

ethanolamine

→

title compound

المردود 91.5%

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

المردود 91.5%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةat reflux for 1.5 h
2. 2
   تركيزthe resulting solution was concentrated under reduced pressure
3. 3
   غسيلThe residue was washed with hexanes
4. 4
   ترشيحfiltered
5. 5
   تركيزthe filtrate was concentrated under reduced pressure
6. 6
   أخرىPurification by flash column chromatography (silica, 10% ethyl acetate/hexanes)

الإجراء التجريبي

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.

المصدر