Pyrazole → HCID 69136279, compound

HRID 1836864Notes

Reaction equation

HRID 1836864 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]2[C:21]([CH2:22]Br)=[CH:20][C:19]3[C:18]([CH3:25])([CH3:24])[CH2:17][CH2:16][C:15]([CH3:27])([CH3:26])[C:14]=3[CH:13]=2)=[CH:6][CH:5]=1.[NH:29]1[CH:33]=[CH:32][CH:31]=[N:30]1>CN1CCCC1.[Cl-].[Na+].O>[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]2[C:21]([CH2:22][N:29]3[CH:33]=[CH:32][CH:31]=[N:30]3)=[CH:20][C:19]3[C:18]([CH3:25])([CH3:24])[CH2:17][CH2:16][C:15]([CH3:27])([CH3:26])[C:14]=3[CH:13]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 1048PyrazoleHCID 23498883Methyl 4-[(1E)-2-[3-(bromomethyl)-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl]ethenyl]benzoate

Product 1

HCID 69136279HCID 69136279, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 84541-MethylpyrrolidineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 2.0 g (4.5 mmol) of (E)-methyl-4-[2-(3-bromomethyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]benzoate and 0.65 g (9.5 mmol) of pyrazole in 15 mL of N-methyl pyrrolidine was heated at 100°. After 2 hours, the reaction mixture 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 stirred with hexane and the product was filtered off, washed with hexane and dried to give 1.6 g (83%) of methyl-4-[2-(5,5,8,8-Tetramethyl-3-pyrazol-1-ylmethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]benzoate (M+=429).

Workup

  1. temperaturewas heated at 100°
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. filtrationthe product was filtered off
  7. washwashed with hexane
  8. customdried

Sources & evidence

ORD record
ord-1e5aab86749748afab1ca9e33bbb9781
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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