p-Toluenesulfonic acid → HCID 15868597, compound

HRID 1596669

Reaction equation

HRID 1596669 reaction equation
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

Participants

6

Reactant 4

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

Product 1

HCID 15868597HCID 15868597, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-73ef1642fb0741b8b5be34d34d6f5756
Source dataset
uspto-grants-2001_09
Patent number
US06291561B1

Linked notes

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