p-Toluenesulfonic acid → HCID 15868597、化合物

HRID 1596669

反応式

HRID 1596669 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:4][C:3]=1[OH:18].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)(O)[C:28]#[CH:29])=[CH:23][CH:22]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C1COCC1>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:18][C:3]3[CH:4]=[C:5]([N:12]4[CH2:17][CH2:16][O:15][CH2:14][CH2:13]4)[C:6]4[C:11]([C:2]=3[CH:29]=[CH:28]2)=[CH:10][CH:9]=[CH:8][CH:7]=4)=[CH:23][CH:22]=1

参加物

6

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 6096921-Chloro-4-morpholin-4-yl-2-naphtholHCID 36948731-(4-Methoxyphenyl)-1-phenylprop-2-yn-1-ol

生成物 1

HCID 15868597HCID 15868597、化合物収率 16.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

0.91 g of 1-chloro-4-morpholino-2-naphthol are allowed to react with 0.95 g of 1-(p-methoxyphenyl)-1-phenyl-2-propyn-1-ol in 30 ml of THF under reflux for 4 hours in the presence of 0.72 g of p-toluene sulfonic acid. The solution is then neutralized with 30 ml of 1N sodium hydroxide and then extracted twice with 30 ml of toluene. The organic phases are evaporated and then the photochrome is separated by chromatography on an alumina column in eluting with a mixture of ethyl acetate/diisopropyl ether (10/90). 250 mg of 3-(p-methoxyphenyl)-3-phenyl-6-morpholino-[3H]-naphtho-[2,1-b]pyran (compound II) are thus obtained. Its structure is confirmed by 1H NMR spectroscopy.

後処理

  1. extractionextracted twice with 30 ml of toluene
  2. customThe organic phases are evaporated
  3. customthe photochrome is separated by chromatography on an alumina column
  4. washin eluting with a mixture of ethyl acetate/diisopropyl ether (10/90)

出典と根拠

ORDレコード
ord-73ef1642fb0741b8b5be34d34d6f5756
出典データセット
uspto-grants-2001_09
特許番号
US06291561B1

関連ノート

読み込み中…