Potassium fluoride dihydrate → HCID 58221469, compound

HRID 575069Notes

Reaction equation

HRID 575069 reaction equation
O.O.[F-].[K+].[CH3:5][N:6]1[CH:10]=[C:9]([C:11]([OH:19])([C:13]#[C:14][Si](C)(C)C)[CH3:12])[N:8]=[CH:7]1>CO>[CH3:5][N:6]1[CH:10]=[C:9]([C:11]([OH:19])([C:13]#[CH:14])[CH3:12])[N:8]=[CH:7]1

Participants

4

Reactant 2

HCID 23708904Potassium fluoride dihydrateHCID 86693097HCID 86693097, compound

Product 1

HCID 58221469HCID 58221469, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Into a 15-mL Schlenk tube, was placed a suspension of potassium fluoride dihydrate (940 mg, 10.00 mmol, 2.50 equiv) and 2-(1-methyl-1H-imidazol-4-yl)-4-(trimethylsilyl)but-3-yn-2-ol (888 mg, 3.99 mmol, 1.00 equiv) in methanol (10 mL). The resulting solution was stirred for 2 h at 50° C. Then most of solvent was concentrated under vacuum and the resulting mixture was diluted with 30 mL of ethyl acetate. The resulting mixture was washed with 2×10 mL of water and 1×10 mL of brine. The mixture was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. This resulted in 255 mg (43%) of 2-(1-methyl-1H-imidazol-4-yl)but-3-yn-2-ol as a gray solid.

Workup

  1. customInto a 15-mL Schlenk tube, was placed
  2. concentrationThen most of solvent was concentrated under vacuum
  3. additionthe resulting mixture was diluted with 30 mL of ethyl acetate
  4. washThe resulting mixture was washed with 2×10 mL of water and 1×10 mL of brine
  5. dry with materialThe mixture was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThis resulted in 255 mg (43%) of 2-(1-methyl-1H-imidazol-4-yl)but-3-yn-2-ol as a gray solid

Sources & evidence

ORD record
ord-f2353df8319242dbae2d08e0e80de7d8
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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