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

HRID 84613

Reaktionsgleichung

Reaktionsgleichung von HRID 84613
[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([O-])(O)=O.[Na+]>C(OCC)C>[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 4

HCID 8000Boron trifluoride etherateHCID 68110ChromanoneHCID 167693TrimethylsilyldiazomethaneHCID 516892Sodium Bicarbonate

Produkt 1

HCID 125800312,3,4,5-Tetrahydro-1-benzoxepin-4-oneAusbeute 42,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 4-chromanone (1 eq, 16.8 mmol, 2.5 g) in anhydrous diethyl ether (70 ml) at 0° C., boron trifluoride diethyl etherate (1.1 eq, 18.6 mmol, 2.4 ml) was added added dropwise followed by the dropwise addition of 2M TMS diazomethane in ether (1.1 eq, 18.6 mmol, 9.2 ml), and stirred at 0° C. under N2 for 1 hr. Saturated NaHCO3 aq was carefully added (100 ml) and the reaction extracted into diethyl ether, the organic layer was then washed with water before drying over MgSO4, filtering and absorbing onto silica. The crude material was then purified on the ISCO companion system running a gradient from 0% ethyl acetate/petrol to 20% ethyl acetate/petrol. This gave 2,3-dihydro-5H-benzo[b]oxepin-4-one as a yellow oil (1.15 g, yield 42%).

Aufarbeitung

  1. additionadded dropwise
  2. extractionthe reaction extracted into diethyl ether
  3. washthe organic layer was then washed with water
  4. dry with materialbefore drying over MgSO4
  5. filtrationfiltering
  6. customabsorbing onto silica
  7. customThe crude material was then purified on the ISCO companion system

Quellen und Nachweise

ORD-Eintrag
ord-1432497e51a044398f4898b002d68085
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846762B2

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