Water → 2-(alpha-Ethoxycarbonyl-4-chlorobenzylidene)-1-isopropylpyrrolidine

HRID 1278032Notes

Reaction equation

HRID 1278032 reaction equation
[Na].[CH2:2]([O:4][C:5](=[O:14])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)[CH3:3].[CH:15]([N+:18]1[CH2:22][CH2:21][CH2:20][C:19]=1N(C)C)([CH3:17])[CH3:16].COS([O-])(=O)=O.O>C(O)C.C(OCC)C>[CH2:2]([O:4][C:5]([C:6](=[C:19]1[CH2:20][CH2:21][CH2:22][N:18]1[CH:15]([CH3:17])[CH3:16])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)=[O:14])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 84177Ethyl (4-chlorophenyl)acetateHCID 5360545SodiumHCID 1784564382-Dimethylamino-1-isopropyl-1-pyrrolinium methyl sulfate

Product 1

HCID 537817902-(alpha-Ethoxycarbonyl-4-chlorobenzylidene)-1-isopropylpyrrolidineYield 8.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Add [dropwise, with stirring, at from 90°-100°, in a stream of nitrogen] a solution of 5.1 g of sodium in 100 ml of ethanol to a mixture of 32 g of 4-chlorophenylacetic acid ethyl ester and 59.13 g of 1-isopropyl-2-dimethylamino-1-pyrrolinium-methylsulfate. After completion of the addition, continue stirring for a further 30 minutes; then cool and take up with water (≈100 ml) and diethyl ether (≈150 ml). Collect the organic phase, extract the aqueous phase once again with diethyl ether, combine the ether extracts, dry and concentrate them to obtain a yield [45.6 g (92% of theory)] of crude title compound; recrystallize 5 g from ethanol/water to obtain 4.2 g of product with a m.p. of 70° to 71°.

Workup

  1. additionAdd [dropwise,
  2. additionAfter completion of the addition
  3. temperaturethen cool
  4. customCollect the organic phase
  5. extractionextract the aqueous phase once again with diethyl ether
  6. customdry
  7. concentrationconcentrate them
  8. customto obtain
  9. customa yield [45.6 g (92% of theory)] of crude title compound
  10. customrecrystallize 5 g from ethanol/water

Sources & evidence

ORD record
ord-ffc96082509f495b8982054b651fb877
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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