Cyclodecanone → diethyl N-(1-cyclodecenyl)-aminomethylenemalonate

HRID 1761527

反応式

HRID 1761527 の反応式
[C:1]1(=O)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:12][CH:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[C:1]1([NH:12][CH:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

参加物

5

反応物 3

HCID 73918CyclodecanoneHCID 226751Diethyl (aminomethylidene)propanedioateHCID 521998p-Toluenesulfonic acid monohydrate

生成物 1

HCID 67906089diethyl N-(1-cyclodecenyl)-aminomethylenemalonate

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

A mixture of 25.0 g of cyclodecanone, 60.7 g of diethyl aminomethylenemalonate, 1.54 g of p-toluenesulfonic acid monohydrate in 500 ml xylene is refluxed 2 weeks under argon, collecting the distillate in a Dean-Stark trap. The solution is then decanted and solvent is removed. The residual oil is triturated twice with hexane and the combined hexane extract is concentrated to yield an oil which is flash chromatographed on 600 g of silica gel using 99:1 methylene chloride ethyl acetate as eluent. A forerun containing cyclodecanone is discarded and the fractions containing the product are combined and concentrated to dryness to give diethyl N-(1-cyclodecenyl)-aminomethylenemalonate as an oil.

後処理

  1. temperatureis refluxed 2 weeks under argon
  2. distillationcollecting the distillate in a Dean-Stark trap
  3. customThe solution is then decanted
  4. customsolvent is removed
  5. customThe residual oil is triturated twice with hexane
  6. extractionthe combined hexane extract
  7. concentrationis concentrated
  8. customto yield an oil which
  9. customchromatographed on 600 g of silica gel using 99:1 methylene chloride ethyl acetate as eluent
  10. additionA forerun containing cyclodecanone
  11. additionthe fractions containing the product
  12. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-192731807edd42b9ba01020ec4633ce5
出典データセット
uspto-grants-1989_05
特許番号
US04826854

関連ノート

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