Tetrabutylammonium Fluoride → 4-(Pyridine-3-carbonyl)-benzyl alcohol

HRID 911710Notes

Reaction equation

HRID 911710 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([C:36]2[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=2)=[O:35])=[CH:30][CH:29]=1)(C(C)(C)C)(C)C>C1COCC1>[N:38]1[CH:39]=[CH:40][CH:41]=[C:36]([C:34]([C:31]2[CH:30]=[CH:29][C:28]([CH2:27][OH:26])=[CH:33][CH:32]=2)=[O:35])[CH:37]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 23302942[4-(tert-Butyldimethylsilyloxymethyl)-phenyl]-pyridin-3-yl-methanone

Product 1

HCID 184620204-(Pyridine-3-carbonyl)-benzyl alcoholYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add tetrabutylammonium fluoride (1.37 mL, 1.37 mmol, 1M solution in THF) to a solution of [4-(tert-butyldimethylsilyloxymethyl)-phenyl]-pyridin-3-yl-methanone (225 mg, 0.687 mmol) in anhydrous THF (10 mL) at 0° C. and stir at this temperature for 1 h. Concentrate the solvent in vacuo and purify the crude mixture by chromatography on silica gel eluting with EtOAc to provide the desired intermediate (85 mg, 58%). MS (ES+) m/z: 214 (M+H)+.

Workup

  1. concentrationConcentrate the solvent in vacuo
  2. custompurify the crude mixture by chromatography on silica gel eluting with EtOAc

Sources & evidence

ORD record
ord-c16476368ae540348559c3f6d1e2cb07
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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