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

HRID 1740110Notes

Reaction equation

HRID 1740110 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].Br[C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([N:20]2[C:24]([CH2:25][CH3:26])=[C:23]([CH2:27]C3C4C(=CC=CC=4)C=CC=3OCC)[C:22]([CH2:41][CH3:42])=[N:21]2)=[C:15]([CH3:43])[CH:14]=1.[CH3:44][C:45]([CH3:47])=[O:46].[O:48]1CC[CH2:50][CH2:49]1>>[CH2:49]([O:48][C:8]1[CH:7]=[CH:6][C:4]2[C:10](=[CH:11][CH:1]=[CH:2][CH:3]=2)[C:9]=1[CH2:27][C:23]1[C:22]([CH2:41][CH3:42])=[N:21][N:20]([C:16]2[C:17]([CH3:19])=[CH:18][C:13]([C:45]([OH:46])([CH3:47])[CH3:44])=[CH:14][C:15]=2[CH3:43])[C:24]=1[CH2:25][CH3:26])[CH3:50]

Participants

6

Reactant 5

HCID 180AcetoneHCID 8028TetrahydrofuranHCID 8058HexaneHCID 218373011-(4-bromo-2,6-dimethylphenyl)4-(2-ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-1H-pyrazoleHCID 178418339Butyllithium

Product 1

HCID 218373502-{4-[4-(2-Ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-pyrazol-1-yl]-3,5-dimethylphenyl}-propan-2-ol

Procedure

To a solution of n-butyl lithium (0.18 ml of a 2.5 M hexane solution, 0.45 mmol) chilled in a dry ice-acetone bath, a solution of 1-(4-bromo-2,6-dimethylphenyl)-4-(2-ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-1H-pyrazole (0.200 g, 0.41 mmol) in 1.0 ml of anhydrous tetrahydrofuran was added dropwise. After stirring for 10 minutes, anhydrous acetone (0.090 ml, 1.23 mmol) was added and the resulting mixture was stirred 10 minutes. The reaction was stirred at ambient temperature for 2 hours before quenching by addition of saturated aqueous ammonium chloride (0.5 ml). The mixture was extracted with ethyl acetate/brine (25 ml of each). The aqueous phase was then extracted twice with 25 ml portions of fresh ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo to an oil (194 mg). Flash chromatography of the entire sample (silica gel, 40 micron mesh; elution with ethyl acetate/hexanes =3:7 in volume) afforded the title compound as a colorless viscous oil (110 mg).

Workup

  1. stirringthe resulting mixture was stirred 10 minutes
  2. stirringThe reaction was stirred at ambient temperature for 2 hours
  3. custombefore quenching by addition of saturated aqueous ammonium chloride (0.5 ml)
  4. extractionThe mixture was extracted with ethyl acetate/brine (25 ml of each)
  5. extractionThe aqueous phase was then extracted twice with 25 ml portions of fresh ethyl acetate
  6. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo to an oil (194 mg)
  8. washFlash chromatography of the entire sample (silica gel, 40 micron mesh; elution with ethyl acetate/hexanes =3:7 in volume)

Sources & evidence

ORD record
ord-669da37722bd493eadad2f1076b87f1e
Source dataset
uspto-grants-1999_10
Patent number
US05968944

Reaction notes

Loading…