Sodium Chloride → 1-(4-Octylphenoxy)-3-(pyrazol-1-yl)propan-2-one

HRID 1821920Notes

Reaction equation

HRID 1821920 reaction equation
C(OC(=O)C)(=O)C.[CH2:8]([C:16]1[CH:31]=[CH:30][C:19]([O:20][CH2:21][CH:22]([OH:29])[CH2:23][N:24]2[CH:28]=[CH:27][CH:26]=[N:25]2)=[CH:18][CH:17]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C(=O)([O-])O.[Na+].[Na+].[Cl-]>CS(C)=O>[CH2:8]([C:16]1[CH:31]=[CH:30][C:19]([O:20][CH2:21][C:22](=[O:29])[CH2:23][N:24]2[CH:28]=[CH:27][CH:26]=[N:25]2)=[CH:18][CH:17]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 129928911-(4-Octylphenoxy)-3-(pyrazol-1-yl)propan-2-ol

Product 1

HCID 99493501-(4-Octylphenoxy)-3-(pyrazol-1-yl)propan-2-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

0.154 g (1.51 mmol) acetic anhydride is mixed with 5 ml absolute DMSO, stirred at room temperature for 10 min and added drop-wise to a solution of 0.050 g (0.152 mmol) 1-(4-octylphenoxy)-3-(pyrazol-1-yl)propan-2-ol in 10 ml absolute DMSO. Having stirred at room temperature for 18 hours, the solution is poured into a mixture of 5% sodium hydrogen carbonate solution and saturated NaCl solution (1:1, v/v) and hydrolyzed for 10 min. Four extractions using diethyl ether, combination of the organic phases, concentration to half the volume on the rotary evaporator, three wash steps with saturated NaCl solution, drying on sodium sulfate, filtration and reconcentration on the rotary evaporator leave as a crude product a yellowish solid which is purified on silica gel by means of column chromatography (flow agent: petroleum ether/ethyl acetate 90:10) and yields the product as a white solid.

Workup

  1. stirringHaving stirred at room temperature for 18 hours
  2. waitv/v) and hydrolyzed for 10 min
  3. extractionFour extractions
  4. concentrationdiethyl ether, combination of the organic phases, concentration to half the volume
  5. customon the rotary evaporator, three
  6. washwash steps with saturated NaCl solution
  7. customdrying on sodium sulfate, filtration and reconcentration on the rotary evaporator
  8. customleave as a crude product a yellowish solid which
  9. customis purified on silica gel by means of column chromatography (flow agent: petroleum ether/ethyl acetate 90:10)

Sources & evidence

ORD record
ord-6a39ced28af84bf2b6f6d0f756936369
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

Loading…