Tetrabutylammonium Fluoride → HCID 58001743, compound

HRID 420742Notes

Reaction equation

HRID 420742 reaction equation
[Cl:1][C:2]1[C:3]([C:17]([OH:20])([CH3:19])[CH3:18])=[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[C:3]([C:17]([OH:20])([CH3:18])[CH3:19])=[N:4][CH:5]=[C:6]([CH2:8][OH:9])[CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58001774HCID 58001774, compound

Product 1

HCID 58001743HCID 58001743, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[3-chloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-2-pyridinyl]-2-propanol (328 mg, 1.038 mmol) in THF (10 ml) was added TBAF (1.557 ml, 1.557 mmol). The solution was stirred at room temperature for 3 h. The mixture was concentrated under vacuum and the residue was purified by Flashmaster chromatography on a 40 g Merk silica gel cartridge using DCM/MeOH 95:5 as eluent to obtain 2-[3-chloro-5-(hydroxymethyl)-2-pyridinyl]-2-propanol (210 mg, 95%) as colourless oil.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customthe residue was purified by Flashmaster chromatography on a 40 g Merk silica gel cartridge

Sources & evidence

ORD record
ord-761ee157d2ba41b29aed08522a17b9ec
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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