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

HRID 2041576Notes

Reaction equation

HRID 2041576 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](=[O:39])[CH2:35][CH:36]([CH3:38])[CH3:37])=[CH:30][N:29]=1)(C(C)(C)C)(C)C>C1COCC1>[OH:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34](=[O:39])[CH2:35][CH:36]([CH3:37])[CH3:38])=[CH:30][N:29]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 576561642-(tert-Butyldimethylsilyloxymethyl)-5-(3-methyl-butyryl)-pyridine

Product 1

HCID 576564172-Hydroxymethyl-5-(3-methyl-butyryl)-pyridineYield 158.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add tetrabutylammonium fluoride (2.13 mL, 2.13 mmol, 1M solution in THF) to a solution of 2-(tert-butyldimethylsilyloxymethyl)-5-(3-methyl-butyryl)-pyridine (330 mg, 1.066 mmol) in anhydrous THF (20 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 (327 mg, 100%).

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-6cef7c68e6d24ede8d5209a125b79236
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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