Pyrazole → 1-(4-Octylphenoxy)-3-(pyrazol-1-yl)propan-2-ol

HRID 1821919Notes

Reaction equation

HRID 1821919 reaction equation
[Na].[NH:2]1[CH:6]=[CH:5][CH:4]=[N:3]1.[CH2:7]([C:15]1[CH:25]=[CH:24][C:18]([O:19][CH2:20][CH:21]2[CH2:23][O:22]2)=[CH:17][CH:16]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[Na+].[Cl-]>C1COCC1>[CH2:7]([C:15]1[CH:16]=[CH:17][C:18]([O:19][CH2:20][CH:21]([OH:22])[CH2:23][N:2]2[CH:6]=[CH:5][CH:4]=[N:3]2)=[CH:24][CH:25]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 1048PyrazoleHCID 5234Sodium ChlorideHCID 107248((p-Octylphenoxy)methyl)oxiraneHCID 5360545Sodium

Product 1

HCID 129928911-(4-Octylphenoxy)-3-(pyrazol-1-yl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

0.091 g (3.96 mmol) sodium is mixed with 5 ml absolute THF and with a solution of 0.268 g (3.94 mmol) pyrazole in 15 absolute THF. Having stirred at room temperature for 2 hours, a solution of 0.690 g (2.63 mmol) 2-(4-octylphenoxymethyl)oxirane in 10 ml THF is added drop-wise and boiled under reflux for 8 hours. The cooled reaction mixture is poured into semi-saturated NaCl solution and extracted four times using diethyl ether. The combined organic phases are concentrated to half the volume on the rotary evaporator. Washing using a semi-saturated NaCl solution, drying on sodium sulfate, filtration and reconcentration on the rotary evaporator leave as a crude product a yellow solid which is purified on silica gel by means of column chromatography (flow agent: petroleum ether/ethyl acetate 85:15) and recrystallized from petroleum ether and yields the product as a white solid.

Workup

  1. temperatureunder reflux for 8 hours
  2. customThe cooled reaction mixture
  3. extractionextracted four times
  4. concentrationThe combined organic phases are concentrated to half the volume
  5. customon the rotary evaporator
  6. washWashing
  7. customdrying on sodium sulfate, filtration and reconcentration on the rotary evaporator
  8. customleave as a crude product a yellow solid which
  9. customis purified on silica gel by means of column chromatography (flow agent: petroleum ether/ethyl acetate 85:15)
  10. customrecrystallized from petroleum ether

Sources & evidence

ORD record
ord-dbfbbdd942b14844a0362176eb5c419a
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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