Tetrabutylammonium Fluoride → HCID 178520927, compound

HRID 585696Notes

Reaction equation

HRID 585696 reaction equation
[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[C@H:23]1[CH2:28][CH2:27][C@H:26]([CH2:29][OH:30])[CH2:25][CH2:24]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:30][CH2:29][C@H:26]1[CH2:25][CH2:24][C@H:23]([C:10]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:9]=2[OH:8])[CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178455049HCID 178455049, compound

Product 1

HCID 178520927HCID 178520927, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

cis/trans-[4-(2,4-Bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexyl]methanol (24 mg) was dissolved in THF (5 ml), and tetrabutylammonium fluoride (0.12 ml, 1.0M in THF) was added. The resulting solution was stirred at room temperature for 15 hr and then partitioned between ethyl acetate (20 ml) and water (2 ml). The aqueous phase was extracted with ethyl acetate (3×20 ml) and the combined organic phases were washed with brine (20 ml), dried over anhydrous magnesium sulphate, and concentrated in vacuo. Purification via flash column chromatography (SiO2 eluting with ethyl acetate:petroleum ether, 1:1 v/v) furnished the desired compound (7 mg, 59%) as a white solid. δH (CD3OD): 0.95-1.06 (0.5H, m), 1.24-1.38 (0.5H, m), 1.43-1.60 (4H, m), 1.69-1.83 (4H, m), 2.62-2.77 (1H, m), 3.30 (1H, d), 3.56 (1H, d), 6.11-6.17 (2H, m), 6.76-7.01 (1H, m); m/z (ES−) 281 (M−1+60)−.

Workup

  1. custompartitioned between ethyl acetate (20 ml) and water (2 ml)
  2. extractionThe aqueous phase was extracted with ethyl acetate (3×20 ml)
  3. washthe combined organic phases were washed with brine (20 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customPurification via flash column chromatography (SiO2 eluting with ethyl acetate:petroleum ether, 1:1 v/v)

Sources & evidence

ORD record
ord-7a14612d6c2546b08331b7902d9da630
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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