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

HRID 1263530Notes

Reaction equation

HRID 1263530 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-d5874217a4094086986188653d29575f
Source dataset
uspto-grants-2003_04
Patent number
US06541473B2

Reaction notes

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