Propanal → 1-{4-[4-(2-Ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-pyrazol-1-yl]-3,5-dimethylphenyl}-propan-1-ol

HRID 1740113Notes

Reaction equation

HRID 1740113 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:13]([CH2:14][CH3:15])=[C:12]([CH2:16][C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][C:18]=3[O:27][CH2:28][CH3:29])[C:11]([CH2:30][CH3:31])=[N:10]2)=[C:4]([CH3:32])[CH:3]=1.[C:33](=[O:35])=O.[CH3:36][C:37](C)=O.C([Li])CCC.C(=O)CC>O1CCCC1.CCCCCC>[CH2:28]([O:27][C:18]1[CH:19]=[CH:20][C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17]=1[CH2:16][C:12]1[C:11]([CH2:30][CH3:31])=[N:10][N:9]([C:5]2[C:6]([CH3:8])=[CH:7][C:2]([CH:33]([OH:35])[CH2:36][CH3:37])=[CH:3][C:4]=2[CH3:32])[C:13]=1[CH2:14][CH3:15])[CH3:29]

Participants

7

Reactant 4

HCID 527PropanalHCID 18522661Acetone cardiceHCID 218373011-(4-bromo-2,6-dimethylphenyl)4-(2-ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-1H-pyrazoleHCID 178418339Butyllithium

Product 1

HCID 218373291-{4-[4-(2-Ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-pyrazol-1-yl]-3,5-dimethylphenyl}-propan-1-ol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 1-(4-bromo-2,6-dimethylphenyl)4-(2-ethoxy-naphthalen-1ylmethyl)-3,5-diethyl-1H pyrazole (0.200 g, 0.41 mmol) in 1.0 ml of anhydrous tetrahydrofuran was added dropwise to a dry ice-acetone both cooled 2.5 M solution of n-butyl lithium (0.179 ml, 0.45 mmol) in hexane. After stirring the reaction mixture 10 minutes, propionaldehyde (0.089 ml, 1.23 mmol) was added. The resulting mixture was stirred 10 minutes, and then removed from the cooling bath and stirred 2 hours. 0.5 ml aqueous saturated ammonium chloride solution was added to quench the reaction. After stirring 10 minutes, the reaction mixture was extracted with methylene chloride/brine (10 ml of each). The aqueous phase was then twice extracted with fresh 10 ml portions of methylene chloride. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo to afford an oil (216 mg). Flash chromatography of the entire sample (silica gel, 40 micron mesh; elution with ethyl acetate/hexanes=3:7 in volume) yielded 133 mg of the title compound as an oil.

Workup

  1. additionwas added
  2. customremoved from the cooling bath
  3. stirringstirred 2 hours
  4. addition0.5 ml aqueous saturated ammonium chloride solution was added
  5. customto quench
  6. customthe reaction
  7. stirringAfter stirring 10 minutes
  8. extractionthe reaction mixture was extracted with methylene chloride/brine (10 ml of each)
  9. extractionThe aqueous phase was then twice extracted with fresh 10 ml portions of methylene chloride
  10. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-33dc0355e38c4bcf8977b867eb2fc820
Source dataset
uspto-grants-1999_10
Patent number
US05968944

Reaction notes

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