HCID 23498916, compound → HCID 23498876, compound

HRID 1836900Notes

Reaction equation

HRID 1836900 reaction equation
C([O:3][C:4](=[O:37])[C:5]1[CH:10]=[CH:9][C:8](/[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])[CH:18]([O:31]C(=O)C)[CH2:17][C:16]([CH3:36])([CH3:35])[C:15]=3[CH:14]=2)=[CH:7][CH:6]=1)C>[Li+].[OH-].C(O)C>[CH3:29][C:19]1([CH3:30])[CH:18]([OH:31])[CH2:17][C:16]([CH3:35])([CH3:36])[C:15]2[CH:14]=[C:13](/[CH:12]=[CH:11]/[C:8]3[CH:7]=[CH:6][C:5]([C:4]([OH:37])=[O:3])=[CH:10][CH:9]=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 23498916HCID 23498916, compound

Product 1

HCID 23498876HCID 23498876, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3939Lithium HydroxideSolvent

Procedure

A mixture of 0.32 g (0.64 mmol) of ethyl-4-[(E)-2-(5,5,8,8-tetramethyl-3pyrazol-1-ylmethyl-6-acetoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]benzoate in 10 mL of 1 N LiOH solution and 20 mL of ethyl alcohol was heated to reflux. After 1 hour the reaction was cooled to room temperature, concentrated under reduced pressure and acidified with 2 N HCl. The aqueous solution was extracted with ethyl acetate, washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/hexane to afford 0.22 g (82%) of 4-[(E)-2-(5,5,8,8-tetramethyl-3pyrazol-1-ylmethyl-6-hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]benzoic acid 55 (mp=241.6-242.0°).

Workup

  1. temperaturewas heated to reflux
  2. concentrationconcentrated under reduced pressure
  3. extractionThe aqueous solution was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-65ae61f465a8404db3d6ca3e90cce4d5
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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