Boron trifluoride etherate → HCID 67069117, compound

HRID 909807Notes

Reaction equation

HRID 909807 reaction equation
[SiH](CC)(CC)CC.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=O)=[C:12]([CH3:25])[CH:11]=1.B(F)(F)F.CCOCC.C(=O)(O)[O-].[Na+]>C(#N)C.C(Cl)(Cl)Cl>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[C:12]([CH3:25])[CH:11]=1

Participants

7

Reactant 4

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 20306642HCID 20306642, compound

Product 1

HCID 67069117HCID 67069117, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

Et3SiH (8.5 mL, 0.0531 mol) was added to a mixed solution of chloroform (8 mL) and acetonitrile (32 mL) of (4-methoxy-2-methyl phenyl)(4-methylphenyl)methanone and BF3.Et2O (4.5 mL, 0.0354 mol) was added dropwise while cooled on ice. The reaction mixture was warmed to room temperature and stirred at 50° C. for one hour. After the reaction mixture was added with a saturated sodium bicarbonate aqueous solution and extracted with ethyl acetate while cooled on ice, the organic phase was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography-(hexane:ethyl acetate=15:1) to obtain colorless oily 4-methoxy-2-methyl-1-(4-methylbenzyl)benzene (3.89 g, 97%).

Workup

  1. additionwas added dropwise
  2. temperaturewhile cooled on ice
  3. extractionextracted with ethyl acetate
  4. temperaturewhile cooled on ice
  5. washthe organic phase was washed with brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. filtrationAfter the desiccant was filtered off
  8. customthe residue obtained
  9. customby evaporating the solvent under reduced pressure
  10. customwas purified by silica gel column chromatography-(hexane:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-46e0e3c1b4c74c539600a5323166f71d
Source dataset
uspto-grants-2011_09
Patent number
US08017792B2

Reaction notes

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