Boron trifluoride etherate → HCID 67304484, compound

HRID 1009878Notes

Reaction equation

HRID 1009878 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([Br:15])=[CH:13][C:12]([CH:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][O:26][CH2:27][O:28][CH3:29])=[CH:20][CH:19]=2)O)=[C:11]([Cl:30])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SiH](CC)(CC)CC.B(F)(F)F.CCOCC.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([Cl:30])[C:12]([CH2:16][C:18]2[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][O:26][CH2:27][O:28][CH3:29])=[CH:22][CH:23]=2)=[CH:13][C:14]=1[Br:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 67304191HCID 67304191, compound

Product 1

HCID 67304484HCID 67304484, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a chloroform solution (8 mL) of [4-(benzyloxy)-5-bromo-2-chlorophenyl][4-[2-(methoxymethoxy)ethyl]phenyl]methanol (750 mg, 1.53 mmol) cooled in ice were added Et3SiH (367 μL, 2.30 mmol) and BF3.Et2O (232 μL, 1.83 mmol), and the mixture was stirred for an hour at the same temperature. To this solution cooled in ice was added a saturated sodium bicarbonate aqueous solution, and warmed to room temperature. The resulting mixture was extracted with ethyl acetate, washed with brine, and dried with anhydrous magnesium sulfate. The drying agent was filtered off, and the solvent was evaporated under reduced pressure. Thus obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain the title compound (290 mg, 40%) as a colorless oily compound.

Workup

  1. temperatureTo this solution cooled in ice
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe solvent was evaporated under reduced pressure
  7. customThus obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-1ebe7ff836b24d93bb548c5438a5d964
Source dataset
uspto-grants-2011_07
Patent number
US07973012B2

Reaction notes

Loading…