Methanol → 4-(1-(2-methyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)butyl)benzoic acid

HRID 537563Notes

Reaction equation

HRID 537563 reaction equation
[CH3:1][C:2]1[CH:23]=[C:22]([N:24]2[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[N:25]2)[CH:21]=[CH:20][C:3]=1[O:4][CH:5]([C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][CH:10]=1)[CH2:6][CH2:7][CH3:8].O.[OH-].[Li+].CO.C1COCC1>O>[CH3:1][C:2]1[CH:23]=[C:22]([N:24]2[CH:28]=[C:27]([C:29]([F:30])([F:32])[F:31])[CH:26]=[N:25]2)[CH:21]=[CH:20][C:3]=1[O:4][CH:5]([C:9]1[CH:19]=[CH:18][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)[CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 68157265ethyl 4-(1-(2-methyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)butyl)benzoate

Product 1

HCID 681566274-(1-(2-methyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)butyl)benzoic acidYield 100.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 4-(1-(2-methyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)butyl)benzoate (90 mg, 0.2 mmol), lithium hydroxide monohydrate (24 mg, 1.0 mmol), methanol (2 ml), THF (3 ml), and water (1 ml) was stirred at +450 for 18 hours. The mixture was concentrated, diluted with 8 ml of water and 2 ml of 1 M potassium hydrogen sulfate. The mixture was extracted with ethyl acetate-heptane (1:1), extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated to obtain the target product as a white solid (84 mg, 99%). MS (M+1): 419.2.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with 8 ml of water and 2 ml of 1 M potassium hydrogen sulfate
  3. extractionThe mixture was extracted with ethyl acetate-heptane (1:1)
  4. extractionextract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-66bedc3bcbac44f3a5b4c104bc96a626
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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