Potassium Carbonate → 4-Ethynyl-1-(2,2,2-trifluoroethyl)-1H-pyrazole

HRID 2205942Notes

Reaction equation

HRID 2205942 reaction equation
[F:1][C:2]([F:16])([F:15])[CH2:3][N:4]1[CH:8]=[C:7]([C:9]#[C:10][Si](C)(C)C)[CH:6]=[N:5]1.C(=O)([O-])[O-].[K+].[K+]>CO>[C:9]([C:7]1[CH:6]=[N:5][N:4]([CH2:3][C:2]([F:15])([F:16])[F:1])[CH:8]=1)#[CH:10]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 682905641-(2,2,2-Trifluoroethyl)-4-((trimethylsilyl)ethynyl)-1H-pyrazole

Product 1

HCID 867063294-Ethynyl-1-(2,2,2-trifluoroethyl)-1H-pyrazoleYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(2,2,2-Trifluoroethyl)-4-((trimethylsilyl)ethynyl)-1H-pyrazole (Preparation 147, 1.19 g) was dissolved in methanol (7 ml) and potassium carbonate (30 mg) was added. The reaction was stirred at room temperature for 3.5 hours. The methanol was evaporated and the residue taken up in dichloromethane (20 ml) and filtered through a plug of silica eluting with DCM to afford the title compound (326 mg, 53%). 1H-NMR (CDCl3, 500 MHz): δ 3.06 (s, 1H), 4.70 (q, J=8.20 Hz, 2H), 7.69 (s, 1H), 7.70 (s, 1H). 19F-NMR (CDCl3, 470.385 MHz): −71.69

Workup

  1. customThe methanol was evaporated
  2. filtrationfiltered through a plug of silica eluting with DCM

Sources & evidence

ORD record
ord-fb6067dfeed74c31b6985cce5654ac31
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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