Methanol → 4-(4-Methoxy-benzyl)-6-methyl-[1,4]oxazepane

HRID 515453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 515453
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[CH2:14][CH:13]([CH3:15])[CH2:12][O:11][CH2:10][C:9]2=O)=[CH:5][CH:4]=1.CO.[OH-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:14][CH:13]([CH3:15])[CH2:12][O:11][CH2:10][CH2:9]2)=[CH:17][CH:18]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 667185484-(4-Methoxy-benzyl)-6-methyl-[1,4]oxazepan-3-one

Produkt 1

HCID 667188184-(4-Methoxy-benzyl)-6-methyl-[1,4]oxazepaneAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 4-(4-methoxy-benzyl)-6-methyl-[1,4]oxazepan-3-one (4.35 g, 17.5 mmol) in tetrahydrofuran (10.0 ml) was added 1M borane-tetrahydrofuran complex in tetrahydrofuran (52.3 ml, 52.3 mmol) at 0° C. The mixture was stirred at room temperature for 4 hours. After cooling to 0° C., methanol (20 ml) and 6N sodium hydroxide aqueous solution (30 ml) was added carefully. The mixture was refluxed for 2 hours and cooled to room temperature. The organic solvent was removed under reduced pressure. The residue was partitioned between saturated ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluant; hexane/ethyl acetate=1/1) to afford 4-(4-methoxy-benzyl)-6-methyl-[1,4]oxazepane as colorless oil (3.24 g, 79%).

Aufarbeitung

  1. temperatureAfter cooling to 0° C.
  2. temperatureThe mixture was refluxed for 2 hours
  3. temperaturecooled to room temperature
  4. customThe organic solvent was removed under reduced pressure
  5. customThe residue was partitioned between saturated ammonium chloride solution and ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography (eluant; hexane/ethyl acetate=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-5ad442450c9c4bcea98fcd936d3082ce
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108957B2

Notizen zur Reaktion

Wird geladen…