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

HRID 2214790Notes

Reaction equation

HRID 2214790 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 solution vent 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 solution vent 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-7b9398866ff140648d098c40bc732a52
Source dataset
uspto-grants-2006_09
Patent number
US07109205B2

Reaction notes

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