Tetrabutylammonium Fluoride → (5-Chloro-6-ethenyl-3-pyridinyl)methanol

HRID 420759Notes

Reaction equation

HRID 420759 reaction equation
[Cl:1][C:2]1[C:3]([CH:17]=[CH2:18])=[N:4][CH:5]=[C:6]([CH2:8][O:9][Si](C(C)(C)C)(C)C)[CH:7]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[N:4][C:3]=1[CH:17]=[CH2:18]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 580017613-Chloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-2-ethenylpyridine

Product 1

HCID 58001738(5-Chloro-6-ethenyl-3-pyridinyl)methanolYield 95.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-chloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-2-ethenylpyridine (707 mg, 2.491 mmol) and TBAF (3.74 ml, 3.74 mmol) in THF (20 ml) was stirred at room temperature overnight. The mixture was concentrated and purified by flash chromatography using Flashmaster II, a 68 g Merck silica gel cartridge, and mixtures of DCM and MeOH as eluent to afford (5-chloro-6-ethenyl-3-pyridinyl)methanol (405 mg, 94%).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-6070ad6a527f492787af27039778b048
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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