Tetrabutylammonium Fluoride → HCID 66618792, compound

HRID 406374Notes

Reaction equation

HRID 406374 reaction equation
[Si]([SiH2][O:19][CH2:20][CH2:21][CH:22]([C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=1)[CH2:23][C:24]#[N:25])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:19][CH2:20][CH2:21][CH:22]([C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:33])([F:34])[F:35])=[CH:28][CH:27]=1)[CH2:23][C:24]#[N:25]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 123763456HCID 123763456, compound

Product 1

HCID 66618792HCID 66618792, compoundYield 107.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(tert-Butyldiphenylsilanylsilanyloxy)-3-(4-trifluoromethylphenyl)pentanenitrile (600 mg) was dissolved in tetrahydrofuran (6 mL), and tetrabutylammonium fluoride (1.5 mL) was added at room temperature. After two hours, the mixture was partitioned with water and ethyl acetate. The organic layer was washed with brine and then dried over magnesium sulfate. Concentration under reduced pressure gave an oil. The oil was purified by silica gel column chromatography (mobile phase:ethyl acetate/heptane=70%) to obtain the title compound (306 mg).

Workup

  1. customthe mixture was partitioned with water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationConcentration under reduced pressure
  5. customgave an oil
  6. customThe oil was purified by silica gel column chromatography (mobile phase:ethyl acetate/heptane=70%)

Sources & evidence

ORD record
ord-df79e97c5e5a4b92adcf5a9537125601
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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