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

HRID 1278032

反応式

HRID 1278032 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 3283Diethyl Ether溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-ffc96082509f495b8982054b651fb877
出典データセット
uspto-grants-1981_07
特許番号
US04279918

関連ノート

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