Methanol → HCID 90950016, compound

HRID 2220637Notes

Reaction equation

HRID 2220637 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[C:5]([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4].[C:18]([O:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[C:29]([CH3:31])[C:28]([C:32]2[CH:37]=[CH:36][C:35](C(=O)C)=[CH:34][CH:33]=2)=[C:27]([CH3:41])[CH:26]=1)(=[O:20])[CH3:19].B(F)(F)F.CCOCC.CO>C(OCC)(=O)C.O.C(Cl)Cl>[CH3:5][O:3][C:1](=[O:4])[CH2:2][C:35]1[CH:34]=[CH:33][C:32]([C:28]2[C:27]([CH3:41])=[CH:26][C:25]([O:24][CH2:23][CH2:22][O:21][C:18](=[O:20])[CH3:19])=[CH:30][C:29]=2[CH3:31])=[CH:37][CH:36]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 8000Boron trifluoride etherateHCID 23134229HCID 23134229, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 90950016HCID 90950016, compoundYield 43.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Lead tetraacetate (1.369 g) was added to an ice-cooled mixture of 1-[4′-(2-acetoxyethoxy)-2′,6′-dimethylbiphenyl-4-yl]ethan-1-one (0.672 g), boron trifluoride diethyl etherate (1.56 mL), methanol (2 mL) and methylene chloride (20 mL) with stirring, and the mixture was stirred at room temperature for 4 hrs. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/2) to afford methyl[4′-(2-acetoxyethoxy)-2′,6′-dimethylbiphenyl-4-yl]acetate (0.318 g).

Workup

  1. temperaturecooled
  2. stirringthe mixture was stirred at room temperature for 4 hrs
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/2)

Sources & evidence

ORD record
ord-9e4945db30ad48fdb0d6cf896114bd8d
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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