Boron trifluoride etherate → HCID 12134925, compound

HRID 348264Notes

Reaction equation

HRID 348264 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[C:5]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[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:30])[C:5]([O:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([CH3:22])[CH2:6][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:10][CH:9]=1)[CH3:2]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 12134921HCID 12134921, compound

Product 1

HCID 12134925HCID 12134925, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(4-Benzyloxyphenyl)-3-hydroxy-2-phenoxy-2-methylpropionic acid ethyl ester (3.84 g, 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 3-(4-benzyloxyphenyl)-2-phenoxy-2-methylpropionic acid ethyl ester as a colorless oil (1.34 g, 36%). Rf=0.90 (9:1 hexanes:ethyl acetate). 1H NMR (300 MHz, CDCl3): δ 7.36–7.42 (m, 3H), 7.34 (t, 1H), 7.17–7.24 (m, 5H), 6.98 (t, 1H), 6.91 (d, 2H), 6.83 (d, 2H), 5.05 (s, 2H), 4.22 (q, 1H, J=7.1), 3.26 (d, 1H, J=13.7), 3.13 (d, 1H, J=13.7), 1.40 (s, 3H), 1.22 (t, 3H, J=7.1). MS [EI+] 408 (M+NH4)+

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-68d740edcc0e402abdc4afa42b0e1a35
Source dataset
uspto-grants-2007_02
Patent number
US07176224B2

Reaction notes

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