Tetrabutylammonium Fluoride → (4-Fluoro-phenyl)-(5-hydroxymethyl-pyridin-3-yl)-methanone

HRID 556273Notes

Reaction equation

HRID 556273 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[CH:9]=[C:10]([C:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[O:15])[CH:11]=[N:12][CH:13]=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:22][C:19]1[CH:18]=[CH:17][C:16]([C:14]([C:10]2[CH:11]=[N:12][CH:13]=[C:8]([CH2:7][OH:6])[CH:9]=2)=[O:15])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178455444HCID 178455444, compound

Product 1

HCID 59200200(4-Fluoro-phenyl)-(5-hydroxymethyl-pyridin-3-yl)-methanoneYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [5-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-3-yl]-(4-fluoro-phenyl)-methanone (1H) (1.7 g, 4.9 mmol) in 20 mL of tetrahydrofuran (THF) at 0° C., is added tetra-butyl-ammonium-fluoride (9.8 mL, 9.9 mmol, 1M in THF) slowly. After being stirred at room temperature for 1 hour, the reaction solution is quenched by addition of 5 mL of water and extracted with 3×10 mL of EtOAc. After concentration, the crude product is purified by chromatography (heptane 80%, EtOAc 20%) to give (4-fluoro-phenyl)-(5-hydroxymethyl-pyridin-3-yl)-methanone (1I) (0.97 g, yield 86%) as white solid. MS (ESI) m/e 232 (M+H+).

Workup

  1. customthe reaction solution is quenched by addition of 5 mL of water
  2. extractionextracted with 3×10 mL of EtOAc
  3. concentrationAfter concentration
  4. customthe crude product is purified by chromatography (heptane 80%, EtOAc 20%)

Sources & evidence

ORD record
ord-62f7c58190fe49bcb33f1158fd45a201
Source dataset
uspto-grants-2011_11
Patent number
US08058272B2

Reaction notes

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