Acetone → HCID 54352560, compound

HRID 1076345Notes

Reaction equation

HRID 1076345 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[CH:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH3:21])=[O:20])=[CH:15][CH:14]=1)[C:7]([CH3:22])=[C:6]2[CH2:23][C:24]([OH:26])=[O:25])#[N:2].[C:27](=[O:30])([O-])[O-].[K+].[K+].[CH3:33]C(C)=O>C(OCC)C>[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[CH:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH3:21])=[O:20])=[CH:15][CH:14]=1)[C:7]([CH3:22])=[C:6]2[CH2:23][C:24]([O:26][CH2:33][O:30][CH3:27])=[O:25])#[N:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 54562088HCID 54562088, compound

Product 1

HCID 54352560HCID 54352560, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Alkoxyalkyl Esters - Chloromethyl methyl ether (0.055 mole) is added to a suspension of 5-cyano-2-methyl-1-(p-methylsulfinylbenzylidene)-3-indenylacetic acid (0.05 mole) and anhydrous potassium carbonate (0.15 mole) in 250 ml. of anhydrous acetone. The mixture is allowed to stir overnight at room temperature. Diethyl ether is added (about 200 ml.) and the mixture is filtered. The filtrate is washed once with 100 ml. of water and dried over anhydrous sodium sulfate. It is then filtered and the solvent is removed in vacuo. The residue is chromatographed on 200 g. of acid-washed alumina, using ether-petroleum ether (varying from 10-60% ether by volume) as the eluent, to give methoxymethyl 5-cyano-2-methyl-1-(p-methylsulfinylbenzylidene)-3-indenylacetate.

Workup

  1. filtrationthe mixture is filtered
  2. washThe filtrate is washed once with 100 ml
  3. dry with materialof water and dried over anhydrous sodium sulfate
  4. filtrationIt is then filtered
  5. customthe solvent is removed in vacuo
  6. customThe residue is chromatographed on 200 g

Sources & evidence

ORD record
ord-381d3b4c99f544b69b74dee78f465cbc
Source dataset
uspto-grants-1976_05
Patent number
US03956363

Reaction notes

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