Potassium Hydroxide → HCID 73507790, compound

HRID 1774558Notes

Reaction equation

HRID 1774558 reaction equation
[C:1]([O:5][CH:6]([C:11]1[N:15]([CH3:16])[N:14]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]=1[C:23]1[CH2:28][CH2:27][C:26]([CH3:30])([CH3:29])[CH2:25][CH:24]=1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>C(O)C.O>[C:1]([O:5][CH:6]([C:11]1[N:15]([CH3:16])[N:14]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]=1[C:23]1[CH2:28][CH2:27][C:26]([CH3:30])([CH3:29])[CH2:25][CH:24]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 90092728HCID 90092728, compound

Product 1

HCID 73507790HCID 73507790, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 2-(tert-butoxy)-2-[4-(4,4-dimethylcyclohex-1-en-1-yl)-1-methyl-3-phenyl-1H-pyrazol-5-yl]acetate (1f) (121 mg, 0.29 mmol) and potassium hydroxide (144 mg, 1.18 mmol) in a mixture of ethanol (1.5 mL) and water (1.5 mL) was refluxed for 6 hours. The reaction mixture was concentrated in vacuo. Water (2 mL) was added to the residue and the aqueous layer was washed with diethyl ether (2×2 mL), acidified with concentrated hydrochloric acid until pH 2 and extracted with diethyl ether (2×3 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to provide 2-(tert-butoxy)-2-[4-(4,4-dimethylcyclohex-1-en-1-yl)-1-methyl-3-phenyl-1H-pyrazol-5-yl]acetic acid (example 1) (101 mg, 0.25 mmol, 86%).

Workup

  1. temperaturewas refluxed for 6 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionWater (2 mL) was added to the residue
  4. washthe aqueous layer was washed with diethyl ether (2×2 mL)
  5. extractionextracted with diethyl ether (2×3 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-956cef604d404079a19b999ea8da948c
Source dataset
uspto-grants-2016_02
Patent number
US09260395B2

Reaction notes

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