Boron trifluoride etherate → trans-2-Benzhydryl-tetrahydropyran-4-ol

HRID 909705

Reaktionsgleichung

[BH3-]C#N.[Na+].[CH:5]([CH:18]1[CH2:23][C:22](=[O:24])[CH:21]=[CH:20][O:19]1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.B(F)(F)F.CCOCC>C1COCC1.CCCCCC.C(OCC)(=O)C>[CH:5]([C@H:18]1[CH2:23][C@H:22]([OH:24])[CH2:21][CH2:20][O:19]1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

NaCNBH3 (0.75 g, 12 mmol) was added portionwise to a mixture of 2-diphenylmethyl-2,3-dihydro-4H-pyran-4-one 2 (1.05 g, 4 mmol) and boron trifluoride etherate (1.99 g, 14 mmol) in dry THF (50 ml) cooled to −78° C. The reaction mixture was allowed to reach room temperature and the reaction was quenched with saturated aqueous NaHCO3 (30 ml). The organic phase was separated, and the aqueous phase was extracted with ethyl ether (3×20 ml). The organic phases were combined and dried over anhydrous Na2SO4. Removal of the solvent under reduced pressure, and purification by flash chromatography (hexane/ethyl acetate 7:3) first afforded trans-2-benzhydryl-tetrahydropyran-4-ol 3a (0.73 g, 68% yield).

Aufarbeitung

customto reach room temperature
customthe reaction was quenched with saturated aqueous NaHCO3 (30 ml)
customThe organic phase was separated
extractionthe aqueous phase was extracted with ethyl ether (3×20 ml)
dry with materialdried over anhydrous Na2SO4
customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag: ord-7bec885c091142e4ad19e0d0b3334900
Quelldatensatz: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08017791B2

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