Pyrazole → HCID 23498916, compound

HRID 1836899Notes

Reaction equation

HRID 1836899 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]2[C:22]([CH2:23]Br)=[CH:21][C:20]3[C:19]([CH3:26])([CH3:25])[CH:18]([O:27][C:28](=[O:30])[CH3:29])[CH2:17][C:16]([CH3:32])([CH3:31])[C:15]=3[CH:14]=2)=[CH:7][CH:6]=1)[CH3:2].[NH:34]1[CH:38]=[CH:37][CH:36]=[N:35]1>CN1CCCC1.[Cl-].[Na+].O>[CH2:1]([O:3][C:4](=[O:33])[C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]2[C:22]([CH2:23][N:34]3[CH:38]=[CH:37][CH:36]=[N:35]3)=[CH:21][C:20]3[C:19]([CH3:26])([CH3:25])[CH:18]([O:27][C:28](=[O:30])[CH3:29])[CH2:17][C:16]([CH3:32])([CH3:31])[C:15]=3[CH:14]=2)=[CH:7][CH:6]=1)[CH3:2]

Participants

5

Reactant 2

HCID 1048PyrazoleHCID 23498913HCID 23498913, compound

Product 1

HCID 23498916HCID 23498916, compoundYield 7,263.6%

Reagents, catalysts & solvents 2

HCID 84541-MethylpyrrolidineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 0.45 g (0.88 mmol) of ethyl-4-[(E)-2-(5,5,8,8-tetramethyl-3-bromomethyl-6-acetoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]benzoate and 0.24 g (3.5 mmol) of pyrazole in 15 mL of N-methyl pyrrolidine was heated to 100° C. After 2 hours the reaction was cooled to room temperature, poured into brine and extracted with ethyl acetate. The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution, hexane-16% ethyl acetate/hexane) to afford 32 g (73%) 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 (M+=500).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (gradient elution, hexane-16% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d69f7d5c2a904c05b5e0c19bdc2ff56f
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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