Lithium hydroxide, monohydrate → HCID 66643734, compound

HRID 1695469Notes

Reaction equation

HRID 1695469 reaction equation
C[O:2][C:3]([C:5]1[N:6]([CH3:25])[N:7]=[C:8](/[CH:10]=[CH:11]\[C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:9]=1)=[O:4].O.[OH-].[Li+]>C1COCC1.O>[F:24][C:21]1[CH:20]=[CH:19][C:18]([C:13]2[C:12](/[CH:11]=[CH:10]\[C:8]3[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[N:6]([CH3:25])[N:7]=3)=[C:16]([CH3:17])[O:15][N:14]=2)=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66643948HCID 66643948, compound

Product 1

HCID 66643734HCID 66643734, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-{(Z)-2-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-yl]-vinyl}-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (6.29 mmol) in THF (14 mL) was added lithium hydroxide monohydrate (37.79 mmol) in water (18 mL) and the resulting mixture stirred for 12 h. After evaporation the mixture was diluted with water (10 mL) and citric acid (10%) and extracted with ethyl acetate (2×80 mL). The combined extracts were then dried with sodium sulfate, filtered and evaporated to afford 5-{(Z)-2-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-yl]-vinyl}-2-methyl-2H-pyrazole-3-carboxylic acid (mg, 85%) as a white solid. MS: m/e=328.2 [M+H]+.

Workup

  1. customAfter evaporation the mixture
  2. additionwas diluted with water (10 mL) and citric acid (10%)
  3. extractionextracted with ethyl acetate (2×80 mL)
  4. dry with materialThe combined extracts were then dried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-207a45c8d7294c87a0e65db65d96a322
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

Loading…