Trifluoroacetic acid → 1-(4-Methyl-1H-pyrazol-1-YL)cyclopropane-1-carboxylic acid

HRID 931063Notes

Reaction equation

HRID 931063 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2([C:10]([O:12]C(C)(C)C)=[O:11])[CH2:9][CH2:8]2)[CH:6]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2([C:10]([OH:12])=[O:11])[CH2:8][CH2:9]2)[CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid3×HCID 117966666tert-butyl 1-(4-methyl-1H-pyrazol-1-yl)cyclopropanecarboxylate

Product 1

HCID 898536841-(4-Methyl-1H-pyrazol-1-YL)cyclopropane-1-carboxylic acidYield 220.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 100 mL pear shaped flask containing tert-butyl 1-(4-methyl-1H-pyrazol-1-yl)cyclopropanecarboxylate (218 mg, 0.981 mmol) were added dichloromethane (5 mL) and trifluoroacetic acid (0.2 mL, 3 mmol). The clear solution was stirred at room temperature for 30 minutes after which another 0.3 mL of trifluoroacetic acid were added. The mixture was stirred at room temperature for 45 minutes and another 0.3 mL of trifluoroacetic acid were added. The mixture was stirred at room temperature for 18 h. The solvent and excess of trifluoroacetic acid were removed under reduced pressure to afford the title compound (360 mg). The material was used without further purification. 1H NMR (400 MHz, CDCl3) δ 1.78 (m, 2H), 2.02 (m, 2H), 2.17 (s, 3H), 7.54 (s, 1H), 7.74 (s, 1H).

Workup

  1. additionwere added
  2. stirringThe mixture was stirred at room temperature for 18 h
  3. customThe solvent and excess of trifluoroacetic acid were removed under reduced pressure

Sources & evidence

ORD record
ord-ea61894d7ae84311a5faf5d8d69304b2
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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