Methanol → 6-Bromo-4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazine

HRID 252358

Reaktionsgleichung

Reaktionsgleichung von HRID 252358
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8](=O)[N:7]([CH2:12][CH2:13][CH2:14][O:15][CH3:16])[C:6]=2[CH:17]=1.CO>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][N:7]([CH2:12][CH2:13][CH2:14][O:15][CH3:16])[C:6]=2[CH:17]=1

Komponenten

4

Edukt 2

HCID 887MethanolHCID 231485196-bromo-4-(3-methoxypropyl)-4H-benzo[1,4]oxazin-3-one

Produkt 1

HCID 669007386-Bromo-4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

The solution of 2.85 g of 6-bromo-4-(3-methoxypropyl)-4H-benzo[1,4]oxazin-3-one in 50 ml of tetrahydrofuran is admixed with 48 ml of 1M borane-tetrahydrofuran complex and stirred at 65° C. over 1 hour. The reaction mixture is cooled to room temperature and then admixed cautiously with 100 ml of methanol. After 10 minutes, the mixture is concentrated to dryness and the title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.31 (1:2 EtOAc-heptane). Rt=4.89 (gradient I).

Aufarbeitung

  1. temperatureThe reaction mixture is cooled to room temperature
  2. waitAfter 10 minutes
  3. concentrationthe mixture is concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-ffc5f95f2600433d842494ae10124080
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868036B2

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