Potassium Fluoride → 2-(5-Fluoropyridin-2-yl)but-3-yn-2-ol

HRID 1398515Notes

Reaction equation

HRID 1398515 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:16])([C:10]#[C:11][Si](C)(C)C)[CH3:9])=[N:6][CH:7]=1.[F-].[K+]>CO.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:16])([C:10]#[CH:11])[CH3:9])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 522689Potassium FluorideHCID 681818642-(5-Fluoropyridin-2-yl)-4-(trimethylsilyl)but-3-yn-2-ol

Product 1

HCID 831252472-(5-Fluoropyridin-2-yl)but-3-yn-2-olYield 86.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(5-fluoropyridin-2-yl)-4-(trimethylsilyl)but-3-yn-2-ol (1 g, 4.21 mmol) and potassium fluoride (987 mg, 16.99 mmol) in methanol (10 mL) was stirred for 2 hr at 50° C. The resulting solution was diluted with ethyl acetate (20 mL) and the solid material was removed by filtration. The filtrate was concentrated in vacuo to give 600 mg (86%) of the title compound as yellow oil: LC-MS: m/z=+166 (M+H)+.

Workup

  1. customthe solid material was removed by filtration
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-aa0eb5df16264d5db4862e46b8e4ea23
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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