Tetrabutylammonium Fluoride → 4-(4-Chloro-phenyl)-4-methoxy-butan-1-ol

HRID 1643308Notes

Reaction equation

HRID 1643308 reaction equation
C([Si]([O:18][CH2:19][CH2:20][CH2:21][CH:22]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)[O:23][CH3:24])(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:31][C:28]1[CH:27]=[CH:26][C:25]([CH:22]([O:23][CH3:24])[CH2:21][CH2:20][CH2:19][OH:18])=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59568823tert-Butyl-[4-(4-chloro-phenyl)-4-methoxy-butoxy]-diphenyl-silane

Product 1

HCID 595687954-(4-Chloro-phenyl)-4-methoxy-butan-1-olYield 74.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl-[4-(4-chloro-phenyl)-4-methoxy-butoxy]-diphenyl-silane (343 mg, 0.75 mmol) in 20 mL THF was added at room temperature TBAF (7.5 mL, 7.5 mmol, 1M in THF). The mixture was stirred for 3 h and the reaction quenched by the addition of 10 mL saturated aqueous NH4Cl. The mixture was extracted with ethyl acetate (3×15 mL) and the combined organic layers washed with brine (2×10 mL) and dried over Na2SO4. The mixture was concentrated and the product isolated by flash column chromatography eluting with 6% to 60% ethyl acetate/hexane to provide 120 mg of the title compound.

Workup

  1. customthe reaction quenched by the addition of 10 mL saturated aqueous NH4Cl
  2. extractionThe mixture was extracted with ethyl acetate (3×15 mL)
  3. washthe combined organic layers washed with brine (2×10 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationThe mixture was concentrated
  6. customthe product isolated by flash column chromatography
  7. washeluting with 6% to 60% ethyl acetate/hexane

Sources & evidence

ORD record
ord-06d9f148be9243c3907ec2bbbc8fdd9f
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

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