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

HRID 606962

Reaction equation

HRID 606962 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

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 5003444Sodium cyanoborohydrideHCID 666308482-Benzhydryl-2H-pyran-4(3H)-one

Product 1

HCID 66631792trans-2-Benzhydryl-tetrahydropyran-4-olYield 68%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

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

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

Sources & evidence

ORD record
ord-13dce756e4584642b572d9229e9ad2c4
Source dataset
uspto-grants-2011_03
Patent number
US07915433B2

Linked notes

Loading…