HCID 23498866, compound → HCID 23498903, compound

HRID 1836905Notes

Reaction equation

HRID 1836905 reaction equation
C[C:2]1[CH:10]=[C:9](/[CH:11]=[CH:12]/[C:13]2[C:22]([CH2:23][N:24]3[CH:28]=[CH:27][CH:26]=[N:25]3)=[CH:21][C:20]3[C:19]([CH3:30])([CH3:29])[C:18](=[O:31])[CH2:17][C:16]([CH3:33])([CH3:32])[C:15]=3[CH:14]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]>CO.[Li+].[OH-]>[CH3:29][C:19]1([CH3:30])[C:18](=[O:31])[CH2:17][C:16]([CH3:32])([CH3:33])[C:15]2[CH:14]=[C:13](/[CH:12]=[CH:11]/[C:9]3[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[CH:2][CH:10]=3)[C:22]([CH2:23][N:24]3[CH:28]=[CH:27][CH:26]=[N:25]3)=[CH:21][C:20]1=2

Participants

4

Reactant 1

HCID 23498866HCID 23498866, compound

Product 1

HCID 23498903HCID 23498903, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3939Lithium HydroxideSolvent

Procedure

A mixture of 0.7 g (1.58 mmol) of methyl-4-[(E)-2-(5,5,8,8-tetramethyl-3-pyrazol-1-ylmethyl-6-oxo -5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]-benzoic acid in 40 ml of MeOH and 20 ml of 1 N LiOH was heated to reflux temperature. After 1 h, the reaction was cooled to room temperature and the MeOH removed under reduced pressure. The aqueous solution was acidified with 2 N HCl, extracted with ethyl acetate, washed with brine, dried over sodium sulfate and adsorbed onto silica gel. The product was purified by flash chromatography (gradient elution: 10-30% ethyl acetate/hexane with 0.2% acetic acid) and by recrystallization (ethyl acetate/hexane) to afford 100 mg (15%) of 4-[(E)-2-(5,5,8,8-tetramethyl-3-pyrazol-1-ylmethyl-6-oxo -5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]-benzoic acid (mp=233-233.5) 133.

Workup

  1. temperaturewas heated
  2. temperatureto reflux temperature
  3. customthe MeOH removed under reduced pressure
  4. extractionextracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe product was purified by flash chromatography (gradient elution: 10-30% ethyl acetate/hexane with 0.2% acetic acid) and by recrystallization (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ecbcb83f9aff40b1a1c3e8a447eb2f88
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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