Tetrabutylammonium Fluoride → HCID 10308268, compound

HRID 895209Notes

Reaction equation

HRID 895209 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[C:19]([N+:23]([O-:25])=[O:24])=[C:18]([OH:26])[CH:17]=[CH:16]3)=[CH:9][CH:8]=1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[C:19]([N+:23]([O-:25])=[O:24])=[C:18]([OH:26])[CH:17]=[CH:16]3)=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 11440850HCID 11440850, compound

Product 1

HCID 10308268HCID 10308268, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-1-nitro-2-naphthol (302 mg, 0.764 mmol) in THF (12 mL) was added TBAF (0.92 mL, 0.917 mmol, 1.0 M solution in THF). The solution was stirred for 10 minutes at room temperature, poured in water. The mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried anhydrous Na2SO4, filtered, evaporation of the solvent, and purification on a silica column (20%-40% ethyl acetate-hexane) yielded 130 mg (61%) of a orange solid. An analytical sample was further purified by recrystallization with ethyl acetate-hexane to yield the title compound as a orange solid:: mp 199-201° C.; 1H NMR (DMDO-d6): δ 6.89(2H, d, J=8.51 Hz), 7.33 (1H, d, J=9.05 Hz), 7.62 (1H, d, J=8.94 Hz), 7.63(2H, d, 8.48 Hz), 7.91 (1H, dd, J=8.87 Hz, J=1.59 Hz), 8.06 (1H, d, 9.18 Hz), 8.17 (1H, d, J=1.31 Hz), 9.64(1H, s), 11.40 (1H,s); MS (ESI) m/z280 (M−H)−.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe combined organic layers were washed with brine, dried anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporation of the solvent, and purification on a silica column (20%-40% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-feb2831b0c034bbd98e74ca07a3fa22a
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

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