Tetrabutylammonium Fluoride → HCID 57421960, compound

HRID 1191985Notes

Reaction equation

HRID 1191985 reaction equation
[Si]([C:8]1[O:9][C:10]2[C:30]([O:31][CH:32]([CH3:34])[CH3:33])=[C:29]([O:35][CH3:36])[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>[CH3:21][O:20][C:18]1[CH:19]=[C:14]([CH:15]=[C:16]([O:24][CH3:25])[C:17]=1[O:22][CH3:23])[C:13]([C:12]1[C:11]2[CH:27]=[CH:28][C:29]([O:35][CH3:36])=[C:30]([O:31][CH:32]([CH3:34])[CH3:33])[C:10]=2[O:9][CH:8]=1)=[O:26]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 24786441HCID 24786441, compound

Product 1

HCID 57421960HCID 57421960, compound

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-7-isopropoxy-benzofuran (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 compound as a light yellow paste (23 mg) that was used directly in the next step; 1H NMR (300 MHz, CDCl3) δ 8.00 (s, 1H, C2H), 7.78 (d, 1H, J=8.60 Hz), 7.15 (s, 2H, benzoyl Hs), 7.04 (d, 1H, J=8.61 Hz), 4.73 (m, 1H), 3.93 (s, 3H, OMe), 3.92 (s, 3H, OMe), 3.90 (s, 6H, 2×OMe), 1.37 (d, 6H, J=6.14 Hz).

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-6064dc5edcc647ae8d9e308db3dc1653
Source dataset
uspto-grants-2014_03
Patent number
US08680135B2

Reaction notes

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