Sodium 3-methoxybenzenethiolate → Ethyl 2-methoxyimino-3-oxo-4-(3-methoxyphenylthio)butyrate

HRID 2412408Notes

Reaction equation

HRID 2412408 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[S-:6].[Na+].[CH3:11][O:12][N:13]=[C:14]([C:20](=[O:23])[CH2:21]Br)[C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(O)C.C(OCC)(=O)C>[CH3:11][O:12][N:13]=[C:14]([C:20](=[O:23])[CH2:21][S:6][C:5]1[CH:7]=[CH:8][CH:9]=[C:3]([O:2][CH3:1])[CH:4]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 2

HCID 11286628Sodium 3-methoxybenzenethiolateHCID 54053279Butanoic acid, 4-bromo-2-(methoxyimino)-3-oxo-, ethyl ester

Product 1

HCID 53867170Ethyl 2-methoxyimino-3-oxo-4-(3-methoxyphenylthio)butyrate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of sodium 3-methoxythiophenoxide in 150 ml of ethanol (prepared by reacting 14 g of 3-methoxythiophenol with 5.94 g of sodium methoxide) were added dropwise over ten minutes 27.7 g of ethyl 2-methoxyimino-3-oxo-4-bromobutyrate. The reaction mixture was stirred at 25° C. for sixteen hours, and then the solvent was removed by evaporation under reduced pressure to give an oil. The oil was dissolved in ethyl acetate and washed several times with water. The organic layer was dried and the solvent was removed by evaporation to afford 16.28 g of ethyl 2-methoxyimino-3-oxo-4-(3-methoxyphenylthio)butyrate. NMR (CDCl3): δ1.32 (t, 3H); δ3.79 (s, 3H); δ4.05 (s, 3H), δ4.34 (q, 2H); δ6.7-7.3 (m, 4H).

Workup

  1. customthe solvent was removed by evaporation under reduced pressure
  2. customto give an oil
  3. washwashed several times with water
  4. customThe organic layer was dried
  5. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-79add22fec9140e1810bca6c48ad4cb5
Source dataset
uspto-grants-1985_01
Patent number
US04492693

Reaction notes

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