Tetrabutylammonium Fluoride → 4-(4-Methylenecyclohexyl)-1,3-benzenediol

HRID 1007978Notes

Reaction equation

HRID 1007978 reaction equation
C([Si]([O:8][C:9]1[CH:14]=[C:13]([O:15][Si](C(C)(C)C)(C)C)[CH:12]=[CH:11][C:10]=1[CH:23]1[CH2:28][CH2:27][C:26](=[CH2:29])[CH2:25][CH2:24]1)(C)C)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:29]=[C:26]1[CH2:27][CH2:28][CH:23]([C:10]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:9]=2[OH:8])[CH2:24][CH2:25]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 17946008Tert-butyl[5-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-methylenecyclohexyl)phenoxy]dimethylsilane

Product 1

HCID 98991634-(4-Methylenecyclohexyl)-1,3-benzenediolYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a round bottomed flask was added tert-butyl[5-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-methylenecyclohexyl)phenoxy]dimethylsilane (40 mg), tetrahydrofuran (2 ml) and tetrabutylammonium fluoride (281 μl, 1.0M in tetrahydrofuran), and the mixture stirred at room temperature for 15 hr. The solvent was removed in vacuo and the residue partitioned between water (20 ml) and ethyl acetate (20 ml). The aqueous phase was extracted with ethyl acetate (2×20 ml), and the combined organic phases were washed with brine (20 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification via flash chromatography (SiO2, ethyl acetate/petroleum ether 2:3 v/v) furnished the title compound (17 mg, 90%) as a white solid. δH (CD3OD): 1.42-1.53 (2H, m), 1.90-1.99 (2H, m), 2.19-2.29 (2H, m), 2.39-2.47 (2H, m), 3.02 (1H, tt), 4.67 (2H, s), 6.28 (1H, dd), 6.31 (1H, d), 6.89 (1H, d); m/z (ES+) 205 (M+H)+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between water (20 ml) and ethyl acetate (20 ml)
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×20 ml)
  4. washthe combined organic phases were washed with brine (20 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification via flash chromatography (SiO2, ethyl acetate/petroleum ether 2:3 v/v)

Sources & evidence

ORD record
ord-28115f07b7ea475d9ca095a037581ba3
Source dataset
uspto-grants-2004_09
Patent number
US06797731B2

Reaction notes

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