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

HRID 1821918Notes

Reaction equation

HRID 1821918 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]=[CH: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:17]=[CH:18][C:19]([O:20][CH2:21][C:22](=[O:29])[CH2:23][N:24]2[CH:28]=[CH:27][CH:26]=[CH:25]2)=[CH:30][CH:31]=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 129928891-(4-Octylphenoxy)-3-(pyrrol-1-yl)propan-2-ol

Product 1

HCID 129928901-(4-Octylphenoxy)-3-(pyrrol-1-yl)propan-2-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

1.24 g (12.1 mmol) acetic anhydride are mixed with 10 ml absolute DMSO, stirred at room temperature for 10 min and added drop-wise to a solution of 0.100 g (0.304 mmol) 1-(4-octylphenoxy)-3-(pyrrol-1-yl)propan-2-ol in 10 ml absolute DMSO. Having stirred for 19 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 with diethyl ether, combination of the organic phases, concentration to half the volume on the rotary evaporator, three wash steps using saturated NaCl solution, drying on sodium sulfate, filtration and reconcentration on the rotary evaporator leave a brownish oil which is purified on silica gel by means of column chromatography (flow agent: petroleum ether/ethyl acetate 97:3) and yields the product as a white solid.

Workup

  1. stirringHaving stirred for 19 hours
  2. waitv/v) and hydrolyzed for 10 min
  3. extractionFour extractions
  4. concentrationwith diethyl ether, combination of the organic phases, concentration to half the volume
  5. customon the rotary evaporator, three
  6. washwash steps
  7. customdrying on sodium sulfate, filtration and reconcentration on the rotary evaporator
  8. customleave a brownish oil which
  9. customis purified on silica gel by means of column chromatography (flow agent: petroleum ether/ethyl acetate 97:3)

Sources & evidence

ORD record
ord-2a7ac3ef7d7044aab53e0c5ea0524818
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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