Boron trifluoride etherate → Methyl 2-hydroxy-3-methoxy-3,3-diphenylpropanoate

HRID 1871276Notes

Reaction equation

HRID 1871276 reaction equation
[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:13][CH:8]2[C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(F)(F)F.C[CH2:25][O:26]CC>CO>[OH:13][CH:8]([C:7]([O:26][CH3:25])([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 10587027Methyl 3,3-diphenyloxirane-2-carboxylate

Product 1

HCID 10541193Methyl 2-hydroxy-3-methoxy-3,3-diphenylpropanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

5 g (19.6 mmol) of methyl 3,3-diphenyl-2,3-epoxypropionate were dissolved in 50 ml of absolute methanol, and, at 0° C., 0.1 ml of boron trifluoride etherate was added. The mixture was stirred at 0° C. for 2 h and at room temperature for a further 12 h. The solvent was removed by distillation, the residue was taken up in ethyl acetate, and the solution was washed with sodium bicarbonate solution and water and dried over magnesium sulfate. After removal of the solvent by distillation, 5.5 g (88%) of a pale yellow oil remained.

Workup

  1. customThe solvent was removed by distillation
  2. washthe solution was washed with sodium bicarbonate solution and water
  3. dry with materialdried over magnesium sulfate
  4. customAfter removal of the solvent
  5. distillationby distillation, 5.5 g (88%) of a pale yellow oil

Sources & evidence

ORD record
ord-9e4d836098bd46b587017e3b6bac489d
Source dataset
uspto-grants-2000_08
Patent number
US06103732

Reaction notes

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