Sodium Methoxide → HCID 70632931, compound

HRID 597454Notes

Reaction equation

HRID 597454 reaction equation
[CH3:1][O-:2].[Na+].[C:4]([C:9]1[CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=1)[NH:12][C:13](=[O:18])/[CH:14]=[C:15](\Cl)/[CH3:16])(=[O:8])[CH2:5][CH2:6][CH3:7]>CO>[C:4]([C:9]1[CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=1)[NH:12][C:13](=[O:18])/[CH:14]=[C:15](\[O:2][CH3:1])/[CH3:16])(=[O:8])[CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86734580HCID 86734580, compound

Product 1

HCID 70632931HCID 70632931, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

5.4 g of sodium methylate were added with stirring to a mixture of 26.5 g of m-butyryl-3-chlorocrotonanilide and 250 ml of methanol and after stirring for 4 hours at 20° C, the mixture was vacuum filtered to remove sodium chloride. The filtrate was concentrated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a 7-3 mixture of benzene and ethyl acetate yielded 14 g of m-butyryl-3-methoxy-crotonanilide melting at 81° C.

Workup

  1. filtrationfiltered
  2. customto remove sodium chloride
  3. concentrationThe filtrate was concentrated to dryness under reduced pressure
  4. customthe residue was chromatographed over silica gel
  5. washElution
  6. additionwith a 7-3 mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-9f09840feab349d9a3d7e0f3e9be17d4
Source dataset
uspto-grants-1977_03
Patent number
US04014679

Reaction notes

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