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p-Toluenesulfonic acid → 3-(p-methoxyphenyl)-3-phenyl-6-morpholino-[3H]-naphtho-[2,1-b]pyran

HRID 1596669
ノート
印刷プレビュー

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 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 158685973-(p-methoxyphenyl)-3-phenyl-6-morpholino-[3H]-naphtho-[2,1-b]pyran収率 16.1%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
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
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06291561B1

反応ノート

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