Sodium Chloride → 1-(Indazol-1-yl)-3-(4-octylphenoxy)propan-2-one

HRID 1821924Notes

Reaction equation

HRID 1821924 reaction equation
C(OC(=O)C)(=O)C.[N:8]1([CH2:17][CH:18]([OH:35])[CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:23][CH:22]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[N:9]1.C(=O)([O-])O.[Na+].[Na+].[Cl-]>CS(C)=O>[N:8]1([CH2:17][C:18](=[O:35])[CH2:19][O:20][C:21]2[CH:22]=[CH:23][C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:25][CH:26]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[N:9]1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 129928931-(Indazol-1-yl)-3-(4-octylphenoxy)propan-2-ol

Product 1

HCID 129928941-(Indazol-1-yl)-3-(4-octylphenoxy)propan-2-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

1.07 g (10.5 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 (0.263 mmol) 1-(indazol-1-yl)-3-(4-octylphenoxy)propan-2-ol in 10 ml absolute DMSO. Having stirred for 20 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 yellow oil 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 for 20 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 yellow oil 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-ae97460021984c178f0018123479190a
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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