Boron trifluoride etherate → p-Tolyloxy-3-(4-benzyloxyphenyl)-2-methyl-propionic acid ethyl ester

HRID 348337Notes

Reaction equation

HRID 348337 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[C:5]([O:23][C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)([CH3:22])[CH:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)O)[CH3:2].B(F)(F)F.CCOCC.C([SiH](CC)CC)C.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:31])[C:5]([O:23][C:24]1[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=1)([CH3:22])[CH2:6][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:13]=1)[CH3:2]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 693536953-(4-Benzyloxyphenyl)-3-hydroxy-2-(p-tolyloxy)-2-methylpropionic acid ethyl ester

Product 1

HCID 69353334p-Tolyloxy-3-(4-benzyloxyphenyl)-2-methyl-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(4-Benzyloxyphenyl)-3-hydroxy-2-(p-tolyloxy)-2-methylpropionic acid ethyl ester (9.5 mmol) in anhydrous CH2Cl2 (30 mL) was cooled to 0° C. and treated with BF3-Et2O (1.16 mL, 9.5 mmol) and triethylsilane (1.51 mL, 9.5 mmol). The mixture was stirred for 2 h and gradually warmed to ambient temperature. Saturated aqueous Na2CO3 (15 mL) was added and the mixture was stirred vigorously. The solution was partitioned and the organic layer was washed twice with water and brine, dried over Na2SO4, and concentrated in vacuo to produce 2-(p-tolyloxy)-3-(4-benzyloxyphenyl)-2-methyl-propionic acid ethyl ester as an oil.

Workup

  1. stirringthe mixture was stirred vigorously
  2. customThe solution was partitioned
  3. washthe organic layer was washed twice with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5a79d0ec002f4288abb747d2ab5159db
Source dataset
uspto-grants-2007_02
Patent number
US07176224B2

Reaction notes

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