Boron trifluoride etherate → 2,3,4,5-Tetrahydro-1-benzoxepin-4-one

HRID 84617

Reaktionsgleichung

Reaktionsgleichung von HRID 84617
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][CH2:2]1.B(F)(F)F.[CH3:16]COCC.[Si](C=[N+]=[N-])(C)(C)C>C(OCC)C.C(=O)(O)[O-].[Na+]>[O:1]1[CH2:2][CH2:3][C:4](=[O:11])[CH2:16][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]1=2

Komponenten

6

Edukt 3

HCID 8000Boron trifluoride etherateHCID 68110ChromanoneHCID 167693Trimethylsilyldiazomethane

Produkt 1

HCID 125800312,3,4,5-Tetrahydro-1-benzoxepin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel3×HCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 4-chromanone (9.54 g, 64.3 mmol) in diethyl ether at 0° C. was slowly added boron trifluoride diethyl etherate (16.3 ml, 128.6 mmol), followed by the dropwise addition of 2M TMSCHN2 in diethyl ether. The mixture was allowed to stir for 1 hour at 0° C. before diluting with sat. sodium bicarbonate solution and diethyl ether. The organic phase was dried, concentrated, and purified on silica to give 2,3-dihydro-5H-benzo[b]oxepin-4-one.

Aufarbeitung

  1. customat 0° C.
  2. customThe organic phase was dried
  3. concentrationconcentrated
  4. custompurified on silica

Quellen und Nachweise

ORD-Eintrag
ord-a84fee2c41ce4e6b9f045d6d307b4e1b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846762B2

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