Ethyl (4-chlorophenyl)acetate → 2-(alpha-Ethoxycarbonyl-4-chlorobenzylidene)-1-methylpyrrolidine

HRID 1278030Notes

Reaction equation

HRID 1278030 reaction equation
[Na].CN(C)[C:4]1[CH2:8][CH2:7][CH2:6][N+:5]=1[CH3:9].COS([O-])(=O)=O.[CH2:17]([O:19][C:20](=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)[CH3:18]>C(O)C>[CH2:17]([O:19][C:20]([C:21](=[C:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH3:9])[C:22]1[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=1)=[O:29])[CH3:18]

Participants

5

Reactant 3

HCID 84177Ethyl (4-chlorophenyl)acetateHCID 5360545SodiumHCID 1784830372-Dimethylamino-1-methyl-1-pyrrolinium methylsulfate

Product 1

HCID 542770622-(alpha-Ethoxycarbonyl-4-chlorobenzylidene)-1-methylpyrrolidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add [dropwise, with stirring, at 100° (bath temperature), in a stream of nitrogen] a solution of 9.6 g of sodium in 200 ml of ethanol to a mixture of 99 g of 2-dimethylamino-1-methyl-1-pyrrolinium-methylsulfate and 65 g of 4-chlorophenylacetic acid ethyl ester. Remove the alcohol from the reaction mixture by the stream of nitrogen. Continue stirring for a further 30 minutes at 100°; cool the reaction mixture; add 200 ml of water to the cooled reaction mixture; and then extract it with 5×100 ml of diethyl ether. Combine the ether extracts, dry the combined extracts over sodium sulfate, concentrate them and then remove a little excess 4-chlorophenylacetic acid ethyl ester by heating under a high vacuum to obtain a yield [86 g (94% of theory)] of crude title compound having a m.p. of 71°.

Workup

  1. additionAdd [dropwise,
  2. customRemove the alcohol from the reaction mixture by the stream of nitrogen
  3. stirringContinue stirring for a further 30 minutes at 100°
  4. temperaturecool the reaction mixture
  5. additionadd 200 ml of water
  6. customto the cooled reaction mixture
  7. extractionand then extract it with 5×100 ml of diethyl ether
  8. dry with materialdry the combined extracts over sodium sulfate
  9. concentrationconcentrate them
  10. customremove a little excess 4-chlorophenylacetic acid ethyl ester
  11. temperatureby heating under a high vacuum
  12. customto obtain

Sources & evidence

ORD record
ord-bd24c06c365440acb8e656c264f27b74
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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