Lithium Hydroxide → HCID 86688731, compound

HRID 1527957Notes

Reaction equation

HRID 1527957 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH3:11])[N:8]([CH2:12][C:13]2[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=2[O:20][CH2:21][C:22]([CH2:26][CH3:27])([CH3:25])[CH2:23][CH3:24])[N:7]=1)=[O:5])C.[Li+].[OH-]>CO.C1COCC1.O>[Br:19][C:17]1[CH:16]=[CH:15][C:14]([O:20][CH2:21][C:22]([CH2:26][CH3:27])([CH3:25])[CH2:23][CH3:24])=[C:13]([CH:18]=1)[CH2:12][N:8]1[C:9]([CH3:11])=[CH:10][C:6]([C:4]([OH:5])=[O:3])=[N:7]1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 86688730HCID 86688730, compound

Product 1

HCID 86688731HCID 86688731, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-[5-bromo-2-(2-ethyl-2-methyl-butoxy)-benzyl]-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester, 22, (0.17 g, 0.38 mmol) in a mixture of MeOH (3 mL) and THF (6 ml) was added a solution of LiOH in 3 ml of H2O. The resulting mixture was heated at 100° C. in an Emrys microwave reactor for 20 minutes. The mixture was poured into water (20 mL) and extracted with EtOAc (3×15 mL). The organic layers were combined, washed with brine (30 mL), dried (MgSO4) and the volatiles were removed in vacuo to yield 1-[5-bromo-2-(2-ethyl-2-methyl-butoxy)-benzyl]-5-methyl-1H-pyrazole-3-carboxylic acid, 23.

Workup

  1. extractionextracted with EtOAc (3×15 mL)
  2. washwashed with brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-fafe70f1116146cc964b4db392599821
Source dataset
uspto-grants-2015_07
Patent number
US09090566B2

Reaction notes

Loading…