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

HRID 1531416Notes

Reaction equation

HRID 1531416 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-ddc7e81e99614c8f9f2634e0ba9f6fe0
Source dataset
uspto-grants-2001_03
Patent number
US06197958B1

Reaction notes

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