Pyrazole → 5,5,8,8-Tetramethyl-3-pyrazol-1-yl-5,6,7,8-tetrahydro-2-naphthaldehyde

HRID 1836885Notes

Reaction equation

HRID 1836885 reaction equation
F[C:2]1[C:3]([CH:16]=[O:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[NH:18]1[CH:22]=[CH:21][CH:20]=[N:19]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:12][C:9]1([CH3:13])[CH2:8][CH2:7][C:6]([CH3:15])([CH3:14])[C:5]2[CH:4]=[C:3]([CH:16]=[O:17])[C:2]([N:18]3[CH:22]=[CH:21][CH:20]=[N:19]3)=[CH:11][C:10]1=2

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 234989783-Fluoro-2-formyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene

Product 1

HCID 234989505,5,8,8-Tetramethyl-3-pyrazol-1-yl-5,6,7,8-tetrahydro-2-naphthaldehydeYield 42.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 0.200 g (0.845 mmol) of 3-fluoro-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthaldehyde, 0.058 g (0.854 mmol) of pyrazole, and 0.130 g (0.939 mmol) of potassium carbonate in 2 mL dimethylsulfoxide was heated to 95° C. for 18 hours. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The product was purified on flash chromatography on silica gel (5% ethyl acetate/hexane) to afford 0.101 g (42%) of 5,5,8,8-tetramethyl-3-pyrazol-1-yl-5,6,7,8-tetrahydro-2-naphthaldehyde. (mp=95.7-97.6).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe product was purified on flash chromatography on silica gel (5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f4bbeca51e6e4266b6ee7c3473525270
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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