3,4-Dimethoxyphenethyl alcohol → Methyl 2-Hydroxy-3-(2-(3,4-dimethoxyphenyl)ethoxy)-3,3-diphenylpropionate

HRID 433926Notes

Reaction equation

HRID 433926 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.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH2:30][CH2:31][OH:32])[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]>ClCCl.B(F)(F)F.CCOCC>[OH:13][CH:8]([C:7]([O:32][CH2:31][CH2:30][C:24]1[CH:25]=[CH:26][C:27]([O:28][CH3:29])=[C:22]([O:21][CH3:20])[CH:23]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 2

HCID 819113,4-Dimethoxyphenethyl alcoholHCID 10587027Methyl 3,3-diphenyloxirane-2-carboxylate

Product 1

HCID 18756198Methyl 2-Hydroxy-3-(2-(3,4-dimethoxyphenyl)ethoxy)-3,3-diphenylpropionate

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalystHCID 6344DichloromethaneSolvent

Procedure

7 g (27.5 mmol) of methyl 3,3-diphenyl-2,3-epoxypropionate and 5.5 g (30.2 mmol) of 2-(3,4-dimethoxyphenyl)ethanol were dissolved in 20 ml of dichloromethane and, at room temperature, 5 drops of boron trifluoride etherate were added. The solution was stirred for 2 hours. The solvent was then distilled off, and the residue (10.7 g, 89%) was immediately reacted further.

Workup

  1. distillationThe solvent was then distilled off
  2. customthe residue (10.7 g, 89%) was immediately reacted further

Sources & evidence

ORD record
ord-25a8cc06e044439baf8afa2a89b389b2
Source dataset
uspto-grants-2003_12
Patent number
US06670367B1

Reaction notes

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