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Pentane → N-(2-Furylethyl)-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline

HRID 26480
ノート
印刷プレビュー

反応式

HRID 26480 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@@:9]23[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]2[C:13](=[O:19])[NH:12][C:11](=[O:20])[CH2:10]3)[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].CCCCC.S(O[CH2:33][CH2:34][C:35]1[O:36][CH:37]=[CH:38][CH:39]=1)(=O)(=O)C>CN(C)C=O>[O:36]1[CH:37]=[CH:38][CH:39]=[C:35]1[CH2:34][CH2:33][N:12]1[C:11](=[O:20])[CH2:10][C@@:9]2([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[C@H:14]([CH2:15][CH2:16][CH2:17][CH2:18]2)[C:13]1=[O:19]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8003PentaneHCID 24758Sodium hydrideHCID 14655779Methanesulfonic acid 2-furan-2-yl-ethyl esterHCID 867364784a-(m-Methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline

生成物 1

HCID 86736481N-(2-Furylethyl)-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒
3 回

実験手順

A solution of 5.0 g (18.5 mmoles) of 4a-(m-methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline in 100 ml of anhydrous dimethylformamide was added to a stirred suspension of 1.4 g (28 mmoles) of 50% sodium hydride in mineral oil (washed with pentane) in 75 ml of anhydrous dimethylformamide heated at 50° under nitrogen. The mixture was heated at 90° for 2 hours, then cooled to 35°. A solution of 7.1 g (37 mmoles) of freshly prepared 2-furylethyl mesylate (prepared according ot the procedure of Crossland and Servis, J. Org. Chem., 35, 3195 (1970)) in 10 ml of anhydrous dimethylformamide was added and the reaction mixture heated at 90° overnight. It was the cooled and poured into ice-water, and extracted with ether. Evaporation of the ether gave an oil which was purified by column chromatography (Silicar CC-7, eluting with acetone-benzene). The major fraction was identified as N-(2-furylethyl)-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline

後処理

  1. temperatureheated at 50° under nitrogen
  2. temperatureThe mixture was heated at 90° for 2 hours
  3. temperaturecooled to 35°
  4. temperaturethe reaction mixture heated at 90° overnight
  5. temperaturecooled
  6. extractionextracted with ether
  7. customEvaporation of the ether
  8. customgave an oil which
  9. customwas purified by column chromatography (Silicar CC-7, eluting with acetone-benzene)

出典と根拠

ORDレコード
ord-add3d012e6f141daa579f8f76fd05db3
出典データセット
uspto-grants-1979_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04150135

反応ノート

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