Boron trifluoride etherate → HCID 20823147, compound

HRID 1393415Notes

Reaction equation

HRID 1393415 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[C:5]([O:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[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:32])[C:5]([O:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=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 69317091HCID 69317091, compound

Product 1

HCID 20823147HCID 20823147, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(4-Benzyloxyphenyl)-2-(4-methoxyphenoxy)-3-hydroxy-2-methylpropionic acid ethyl ester (2.15 g, 4.9 mmol) in anhydrous CH2Cl2 (30 mL) was cooled to 0° C. and treated with BF3-Et2O (0.91 mL, 7.4 mmol, d=1.154) and triethylsilane (1.18 mL, 7.4 mmol, d=0.728). The mixture was stirred for 2 h, gradually warming 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-benzyloxy-phenyl)-2-(4-methoxyphenoxy)-2-methylpropionic acid ethyl ester as a colorless oil (428 mg, 21%). Rf=0.36 in 4:1 hexanes:ethyl acetate 1H NMR (300 MHz, CDCl3): δ 7.45 (t, 2H, J=7.1), 7.35 (d, 2H, J=7.1), 7.34 (t, 1H, J=7.0), 7.18 (d, 2H, 8.6), 6.91 (d, 2H, J=6.6), 6.79 (d, 2H, 8.6), 6.74 (d, 2H, J=6.6), 5.05 (s, 2H), 4.21 (q, 1H, J=7.1), 3.75 (s, 3H), 3.23 (d, 1H, J=13.7), 3.10 (d, 1H, J=13.7), 1.31 (s, 3H), 1.25 (t, 3H, J=7.1). MS [EI+] 438 (M+NH4)+, [EI−] 419 (M−H)+.

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-a373d14690264a9580d3f4385969d44a
Source dataset
uspto-grants-2008_03
Patent number
US07345070B2

Reaction notes

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