Water → 3,5-Diphenyl-1-(prop-2-en-1-yl)-4-propoxy-1H-pyrazole

HRID 1576253Notes

Reaction equation

HRID 1576253 reaction equation
[C:1]1([C:7]2[C:11]([O:12][CH2:13][CH2:14][CH3:15])=[C:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:22][C:23](C)([O-])[CH3:24].[K+].BrCC=C.O>CC(O)C>[CH2:24]([N:8]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:11]([O:12][CH2:13][CH2:14][CH3:15])[C:10]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[N:9]1)[CH:23]=[CH2:22]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 213980993,5-Diphenyl-4-propoxy-1H-pyrazoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 215144723,5-Diphenyl-1-(prop-2-en-1-yl)-4-propoxy-1H-pyrazoleYield 55%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

3,5-Diphenyl-4-n-propoxypyrazole (9.0 g, 0.038 mole) is dissolved in 2-propanol (90 ml). Potassium t-butoxide (4.65 g, 0.042 mole) is added at room temperature and the reaction mixture stirred and heated at 50°C for 3 hours. It is then cooled to room temperature and 3-bromoprop-1-ene (5.53 g, 0.046 mole) is added dropwise. A white solid forms. Stirring is continued at room temperature overnight, the mixture is then poured into water and extracted with chloroform. The chloroform layer is washed with water (3 × 150 ml) and stripped under vacuum. The residual oil is purified by dry column chromatography (silica gel/toluene). The toluene solution is stripped under vacuum to afford 6.64 g (55%) product.

Workup

  1. temperatureIt is then cooled to room temperature
  2. stirringStirring
  3. extractionextracted with chloroform
  4. washThe chloroform layer is washed with water (3 × 150 ml)
  5. customThe residual oil is purified
  6. customby dry column chromatography (silica gel/toluene)

Sources & evidence

ORD record
ord-4000302488814b80a6872da428834eab
Source dataset
uspto-grants-1976_09
Patent number
US03979409

Reaction notes

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