Carbon Dioxide → 1-cyclopentyl-1H-pyrazole-4-carboxylic acid

HRID 1930391Notes

Reaction equation

HRID 1930391 reaction equation
Br[C:2]1[CH:3]=[N:4][N:5]([CH:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=1.[Li]CCCC.[C:17](=[O:19])=[O:18]>>[CH:7]1([N:5]2[CH:6]=[C:2]([C:17]([OH:19])=[O:18])[CH:3]=[N:4]2)[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 3

HCID 280Carbon DioxideHCID 518921224-bromo-1-cyclopentyl-1H-pyrazoleHCID 178418339Butyllithium

Product 1

HCID 196200201-cyclopentyl-1H-pyrazole-4-carboxylic acidYield 47%

Procedure

Using the procedure of Example B30, 4-bromo-1-cyclopentyl-1 H-pyrazole (9.0 g, 42 mmol), n-BuLi (2.5 M, 18.5 mL, 46.2 mmol) and CO2 were combined to provide 1-cyclopentyl-1 H-pyrazole-4-carboxylic acid (3.5 g, 47% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.31 (s, 1H), 7.85 (s, 1 H), 4.78 (m, 1 H), 1.70-2.56 (m, 8 H); MS (ESI) m/z: 181.1 [M+H]+.

Sources & evidence

ORD record
ord-0e9c8ddc3f6847a29c331ba89afa0102
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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