Tetrabutylammonium Fluoride → 3-(3,4,5-Trimethoxybenzoyl)-6-methoxy-benzofuran

HRID 1020476Notes

Reaction equation

HRID 1020476 reaction equation
[Si]([C:8]1[O:9][C:10]2[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:11]=2[C:12]=1[C:13](=[O:26])[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[CH3:25][O:24][C:16]1[CH:15]=[C:14]([CH:19]=[C:18]([O:20][CH3:21])[C:17]=1[O:22][CH3:23])[C:13]([C:12]1[C:11]2[CH:27]=[CH:28][C:29]([O:31][CH3:32])=[CH:30][C:10]=2[O:9][CH:8]=1)=[O:26]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 247872412-t-Butyldimethylsilyl-3-(3,4,5-trimethoxybenzoyl)-6-methoxy-benzofuran

Product 1

HCID 247866663-(3,4,5-Trimethoxybenzoyl)-6-methoxy-benzofuranYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-t-butyldimethylsilyl-3-(3,4,5-trimethoxy-benzoyl)-6-methoxy-benzofuran (30 mg, 0.066 mmol) in tetrahydrofuran (1 mL) was added tetrabutylammoniumfluoride (76.5 μL, 0.076 mmol, 1M solution in tetrahydrofuran). The reaction mixture was stirred at room temperature for 20 minutes (monitored by tlc), diluted with ethyl acetate (10 mL) and washed with 1M hydrochloric acid (5 mL). The organic layer was dried over magnesium sulfate and the solvent was removed under vacuum. The crude product was purified by flash chromatography (silica gel, eluent=hexane/diethyl ether; 7:3) to afford the title product as a cream crystalline solid (19.3 mg, 86%); 1H NMR (300 MHz, CDCl3) δ 8.02 (d, 1H, J=8.97 Hz), 8.01 (s, 1H, C2H), 7.14 (s, 2H, benzoyl Hs), 7.05 (d, 1H, J=2.11 Hz), 7.00 (dd, 1H, J=8.63, 2.11 Hz), 3.93 (s, 3H, OMe), 3.90 (s, 6H, 2×OMe), 3.87 (s, 3H, OMe); 13C NMR (75 MHz, CDCl3) δ 188.71 (CO), 158.64, 156.31, 152.82, 150.22, 141.72, 133.97, 122.58, 120.87, 118.12, 113.11, 106.07, 95.53, 60.63, 55.99, 55.40.

Workup

  1. washwashed with 1M hydrochloric acid (5 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customthe solvent was removed under vacuum
  4. customThe crude product was purified by flash chromatography (silica gel, eluent=hexane/diethyl ether; 7:3)

Sources & evidence

ORD record
ord-0356aa4e97484806aeacaaf1f5130711
Source dataset
uspto-grants-2014_05
Patent number
US08716335B2

Reaction notes

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