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

HRID 251400Notes

Reaction equation

HRID 251400 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-b47188d8c56d48d5a3f02cb84aa83f9b
Source dataset
uspto-grants-2011_01
Patent number
US07863445B2

Reaction notes

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