Potassium Hydroxide → HCID 73603425, compound

HRID 1774581Notes

Reaction equation

HRID 1774581 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][N:18]=2)[C:12]=1[C:23]1[CH:24]=[CH:25][C:26]2[O:31][CH2:30][CH2:29][CH2:28][C:27]=2[CH:32]=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][N:18]=2)[C:12]=1[C:23]1[CH:24]=[CH:25][C:26]2[O:31][CH2:30][CH2:29][CH2:28][C:27]=2[CH:32]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 118389598HCID 118389598, compound

Product 1

HCID 73603425HCID 73603425, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 2-(tert-butoxy)-2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-1-methyl-3-(pyridin-2-yl)-1H-pyrazol-5-yl]acetate (9h) (58 mg, 0.13 mmol) and potassium hydroxide (65 mg, 0.53 mmol) in a mixture of ethanol (1.0 mL) and water (1.0 mL) was refluxed overnight. The mixture was concentrated in vacuo. Water (2 mL) was added to the residue and the aqueous layer was washed with diethyl ether (2 mL), acidified with 1M hydrochloric acid until pH 3 and extracted with ethyl acetate (2×3 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to provide 2-(tert-butoxy)-2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-1-methyl-3-(pyridin-2-yl)-1H-pyrazol-5-yl]acetic acid (example 9) (32 mg, 0.076 mmol, 57%).

Workup

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

Sources & evidence

ORD record
ord-70e831c62fab4cfc848c544c04753219
Source dataset
uspto-grants-2016_02
Patent number
US09260395B2

Reaction notes

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