Potassium Hydroxide → HCID 57826771, compound

HRID 2392261Notes

Reaction equation

HRID 2392261 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([O:9]C)=[O:8])=[CH:4][C:3]=1[C:11]1[N:15]([CH2:16][CH3:17])[N:14]=[CH:13][C:12]=1[CH3:18].[OH-].[K+]>C1COCC1.O>[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][C:3]=1[C:11]1[N:15]([CH2:16][CH3:17])[N:14]=[CH:13][C:12]=1[CH3:18]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 57826796Methyl 5-chloro-4-(1-ethyl-4-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate

Product 1

HCID 57826771HCID 57826771, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 5-chloro-4-(1-ethyl-4-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (260 mg, 0.90 mmol) in THF/H2O (2 mL/2 mL) was added KOH (201 mg, 3.6 mmol). The reaction mixture was heated to 50° C. for 4 h. After the mixture was concentrated and diluted with H2O, the pH was adjusted to 3. The mixture was extracted with DCM (5 mL×3). The collected organic layers were concentrated under vacuum to give crude 5-chloro-4-(1-ethyl-4-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic acid, which was used directly without further purification: LC-MS (ES) m/z 271 (M+H)+.

Workup

  1. concentrationAfter the mixture was concentrated
  2. additiondiluted with H2O
  3. extractionThe mixture was extracted with DCM (5 mL×3)
  4. concentrationThe collected organic layers were concentrated under vacuum

Sources & evidence

ORD record
ord-7b309f1df78c4d67b44f7308cfaa7eec
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

Loading…