Tetrabutylammonium Fluoride → 5-Hydroxymethyl-2-(3-methyl-butyryl)-pyridine

HRID 2041579Notes

Reaction equation

HRID 2041579 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][C:28]1[CH:29]=[CH:30][C:31]([C:34](=[O:39])[CH2:35][CH:36]([CH3:38])[CH3:37])=[N:32][CH:33]=1)(C(C)(C)C)(C)C>C1COCC1>[OH:26][CH2:27][C:28]1[CH:29]=[CH:30][C:31]([C:34](=[O:39])[CH2:35][CH:36]([CH3:37])[CH3:38])=[N:32][CH:33]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 576559115-(tert-Butyldimethylsilyloxymethyl)-2-(3-methyl-butyryl)-pyridine

Product 1

HCID 576561925-Hydroxymethyl-2-(3-methyl-butyryl)-pyridineYield 84.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add tetrabutylammonium fluoride (5.853 mL, 5.853 mmol, 1M solution in THF) to a solution of 5-(tert-butyldimethylsilyloxymethyl)-2-(3-methyl-butyryl)-pyridine (900 mg, 2.927 mmol) in anhydrous THF (30 mL) at 0° C. and stir at this temperature for 2 h. Concentrate the solvent in vacuo and purify the crude mixture by chromatography on silica gel eluting with hexane and hexane/EtOAc (3:2) to provide the desired intermediate (478 mg, 84%). MS (ES+) m/z: 194 (M+H)+.

Workup

  1. concentrationConcentrate the solvent in vacuo
  2. custompurify the crude mixture by chromatography on silica gel eluting with hexane and hexane/EtOAc (3:2)

Sources & evidence

ORD record
ord-3137ee78dcc54254ba5302f6fe0f8e9d
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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