p-Toluenesulfonic acid → HCID 15868597, 화합물

HRID 1596669

반응식

HRID 1596669 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 15868597HCID 15868597, 화합물수율 16.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-73ef1642fb0741b8b5be34d34d6f5756
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06291561B1

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