Reaktion #42465

Reaktionsgleichung

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

9-BBN

ethanolamine

→

title compound

Ausbeute 91.5%

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

Ausbeute 91.5%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 1.5 h
2. 2
   Einengenthe resulting solution was concentrated under reduced pressure
3. 3
   WaschenThe residue was washed with hexanes
4. 4
   Filtrationfiltered
5. 5
   Einengenthe filtrate was concentrated under reduced pressure
6. 6
   SonstigePurification by flash column chromatography (silica, 10% ethyl acetate/hexanes)

Vorschrift

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.

Quelle