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

HRID 1359519Notes

Reaction equation

HRID 1359519 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 distilled out, the residue was taken up in ethyl acetate, washed with sodium bicarbonate solution and water and dried over magnesium sulfate. After removal of the solvent by distillation there remained 5.5 g (88%) of a pale yellow oil.

Workup

  1. distillationThe solvent was distilled out
  2. washwashed with sodium bicarbonate solution and water
  3. dry with materialdried over magnesium sulfate
  4. customAfter removal of the solvent
  5. distillationby distillation there remained 5.5 g (88%) of a pale yellow oil

Sources & evidence

ORD record
ord-1b03c13da79348dc96bb81447a48e0f4
Source dataset
uspto-grants-2003_07
Patent number
US06600043B2

Reaction notes

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