Methanol → Cyclohexanecarbonitrile, 1-(3,4-dimethoxyphenyl)-4-oxo-

HRID 1905561ノート

反応式

HRID 1905561 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:24]#[N:25])([CH2:18][CH2:19][C:20]([O:22]C)=O)[CH2:12][CH2:13]C(OC)=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Na+].CO>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([C:24]#[N:25])[CH2:12][CH2:13][C:20](=[O:22])[CH2:19][CH2:18]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

参加物

5

反応物 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 1803855Dimethyl 4-cyano-4-(3,4-dimethoxyphenyl)heptanedioate

生成物 1

HCID 749913Cyclohexanecarbonitrile, 1-(3,4-dimethoxyphenyl)-4-oxo-

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
25 °C

実験手順

A solution of dimethyl 4-(3,4-dimethoxyphenyl)-4-cyanopimelate (11.2 g, 32.1 mmol), sodium hydride (2.31 g, 48.1 mmol) and methanol (1 ml) in 250 ml anhydrous toluene was heated at reflux for 10 hours, cooled to 25° C., quenched with 4 ml acetic acid, washed with H2O, alkali, and brine and dried with MgSO4. The volatiles were removed in vacuo. The residue was recrystallized with hexanes-ethyl acetate. This intermediate was heated at reflux in ethanol, concentrated HCl and 25% aqueous H2SO4 for 10 hours. The volatiles were removed in vacuo. The residue was diluted with water and extracted with ether. The combined organic extracts were washed with water, brine and dried (MgSO4). The volatiles were removed in vacuo. The residue was recrystallized with toluene and then with hexanes-ethyl acetate, mp 111°-12° C. ##STR5##

後処理

  1. temperatureat reflux for 10 hours
  2. customquenched with 4 ml acetic acid
  3. washwashed with H2O
  4. dry with materialbrine and dried with MgSO4
  5. customThe volatiles were removed in vacuo
  6. customThe residue was recrystallized with hexanes-ethyl acetate
  7. temperatureThis intermediate was heated
  8. temperatureat reflux in ethanol
  9. customThe volatiles were removed in vacuo
  10. additionThe residue was diluted with water
  11. extractionextracted with ether
  12. washThe combined organic extracts were washed with water, brine
  13. dry with materialdried (MgSO4)
  14. customThe volatiles were removed in vacuo
  15. customThe residue was recrystallized with toluene

出典と根拠

ORDレコード
ord-57f1090436914d2fb246ff93ae6fb8cd
出典データセット
uspto-grants-1989_06
特許番号
US04843081

反応ノート

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