Acetone → HCID 14699421, compound

HRID 1073772Notes

Reaction equation

HRID 1073772 reaction equation
[OH:1][CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5](=[O:13])[C:4]2[CH:14]=[CH:15][N:16]=[CH:17][C:3]1=2.CC(C)=O.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(=O)([O-])O.[Na+]>CN(C)C=O.CO>[CH:17]1[C:3]2[C:2](=[O:1])[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[NH:6][C:5](=[O:13])[C:4]=2[CH:14]=[CH:15][N:16]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 516892Sodium BicarbonateHCID 14699420HCID 14699420, compoundHCID 131709961Jones' reagent

Product 1

HCID 14699421HCID 14699421, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

In 190 ml of dimethylformamide was dissolved 8 g (79.6 mmol) of the compound (6a). To the solution was added 250 ml of acetone, and 19 ml of 4N Jones' reagent was then added thereto dropwise at room temperature. After the mixture was stirred at room temperature for 30 minutes, 100 ml of methanol and excess sodium hydrogencarbonate were added thereto. The solvent was removed by distillation under reduced pressure. To the residue was added 200 ml of water, and the precipitated crystals were collected by filtration to obtain the entitled compound (II-1) in a yield of 9.7 g (54.5%).

Workup

  1. additionwas then added
  2. customdropwise at room temperature
  3. customThe solvent was removed by distillation under reduced pressure
  4. additionTo the residue was added 200 ml of water
  5. filtrationthe precipitated crystals were collected by filtration
  6. customto obtain the entitled compound (II-1) in a yield of 9.7 g (54.5%)

Sources & evidence

ORD record
ord-017c4b75b8174b74a5266b029de69540
Source dataset
uspto-grants-1990_11
Patent number
US04971964

Reaction notes

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