Boron trifluoride etherate → HCID 54471461, compound

HRID 1713576Notes

Reaction equation

HRID 1713576 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=O)=[CH:5][CH:4]=1)[CH3:2].C([SiH](CC)CC)C.B(F)(F)F.CCOCC>C(#N)C.C(Cl)Cl>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)=[CH:5][CH:4]=1)[CH3:2]

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 12343547(4-Ethylphenyl)(4-methoxyphenyl)methanone

Product 1

HCID 54471461HCID 54471461, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (4-ethylphenyl)(4-methoxyphenyl)methanone (1) (6.0 g, 25 mmol) in acetonitrile (50 mL) and DCM (50 mL) at 0° C., was added triethylsilane (6.7 g, 57.5 mmol), followed by addition of boron trifluoride etherate (5.3 g, 37.5 mmol). The reaction mixture was stirred at 0° C. for 2 h, then at 50° C. for 3 h. After cooling to rt, the reaction mixture was diluted with DCM (500 mL) and washed with 2N aqueous NaOH (200 mL×2), brine (200 mL×3), dried over MgSO4 and evaporated to give product as a colorless oil, 5.3 g, yield 93.7% 1H NMR (300 MHz, CDCl3) δ 7.06-7.09 (m, 6H), 6.79 (d, J=8.7 Hz, 2H), 3.87 (s, 2H), 3.76 (s, 3H), 2.60 (q, J=7.5 Hz, 2H), 1.21 (t, J=7.5 Hz, 3H).

Workup

  1. waitat 50° C. for 3 h
  2. temperatureAfter cooling to rt
  3. washwashed with 2N aqueous NaOH (200 mL×2), brine (200 mL×3)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customto give product as a colorless oil, 5.3 g, yield 93.7% 1H NMR (300 MHz, CDCl3) δ 7.06-7.09 (m, 6H), 6.79 (d, J=8.7 Hz, 2H), 3.87 (s, 2H), 3.76 (s, 3H), 2.60 (q, J=7.5 Hz, 2H), 1.21 (t, J=7.5 Hz, 3H)

Sources & evidence

ORD record
ord-d4eac7be265b4082adbfe7df755acd00
Source dataset
uspto-grants-2010_09
Patent number
US07795228B2

Reaction notes

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