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

HRID 78888Notes

Reaction equation

[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

Participants

Conditions

Temperature: -78 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-ec2926626b8f419e84c676de1793e7c2
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841464B2

Reaction notes

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