Tetrabutylammonium Fluoride → HCID 57421960, compound

HRID 529239Notes

Reaction equation

HRID 529239 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-528eb8a6c5574e02b6660181d2e03f0e
Source dataset
uspto-grants-2016_05
Patent number
US09346842B2

Reaction notes

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