Methanol → HCID 22943903, compound

HRID 705329Notes

Reaction equation

HRID 705329 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]3[O:25][CH2:24]3)=[CH:17][CH:16]=2)([CH3:14])[CH3:13])=[CH:8][CH:7]=1)[CH:2]1[O:4][CH2:3]1.FC(F)(F)S([O-])(=O)=O.[Er+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.C(=O)(O)[O-].[Na+].[CH3:56][OH:57]>>[CH3:56][O:57][CH2:24][CH:23]([OH:25])[CH2:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:1][CH:2]3[CH2:3][O:4]3)=[CH:7][CH:8]=2)([CH3:14])[CH3:13])=[CH:16][CH:17]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 2286Bisphenol A diglycidyl etherHCID 516892Sodium BicarbonateHCID 11479047Erbium(III) trifluoromethanesulfonate

Product 1

HCID 22943903HCID 22943903, compoundYield 23%

Procedure

To a solution of racemic derivative Bisphenol A diglycidyl ether (500 mg, 1.46 mmol, 1 equiv) in methanol (5 mL) was added solid Erbium(III) trifluoromethanesulfonate (90 mg, 0.146 mmol, 1/10 equiv) in one portion and the mixture was stirred at room temperature for 1 h. Sodium bicarbonate was added (1 mL), the organic solvent was evaporated under reduced pressure and the residue was extracted with dichloromethane (3×5 mL). The organic layer was washed with deionized water (2×5 mL), was dried over anhydrous magnesium sulfate, was filtered, and was concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel (eluent: 10% to 40% ethyl acetate in hexane) to provide the title compound (128 mg, 23%) as a pale foam.

Workup

  1. customthe organic solvent was evaporated under reduced pressure
  2. extractionthe residue was extracted with dichloromethane (3×5 mL)
  3. washThe organic layer was washed with deionized water (2×5 mL)
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationwas filtered
  6. concentrationwas concentrated under reduced pressure
  7. customThe resulting residue was purified by flash column chromatography on silica gel (eluent: 10% to 40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-89624e5c0114478c86782ac509724b84
Source dataset
uspto-grants-2015_11
Patent number
US09173939B2

Reaction notes

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