Methyl 1,4-dihydroxy-2-naphthoate → Methyl 2-(4-diethylaminophenyl)-6-hydroxy-2-phenyl-2H-naphtho[1,2-b]pyran-5-carboxylate

HRID 2369641Notes

Reaction equation

HRID 2369641 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][C:3]=1[C:13]([O:15][CH3:16])=[O:14].[CH2:17]([N:19]([CH2:36][CH3:37])[C:20]1[CH:25]=[CH:24][C:23]([C:26]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)(O)[C:27]#[CH:28])=[CH:22][CH:21]=1)[CH3:18]>C1(C)C=CC=CC=1>[CH2:36]([N:19]([CH2:17][CH3:18])[C:20]1[CH:25]=[CH:24][C:23]([C:26]2([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[O:12][C:5]3[C:6]4[C:11]([C:2]([OH:1])=[C:3]([C:13]([O:15][CH3:16])=[O:14])[C:4]=3[CH:28]=[CH:27]2)=[CH:10][CH:9]=[CH:8][CH:7]=4)=[CH:22][CH:21]=1)[CH3:37]

Participants

4

Reactant 2

HCID 604167Methyl 1,4-dihydroxy-2-naphthoateHCID 155368361-(4-Diethylaminophenyl)-1-phenyl-prop-2-yn-1-ol

Product 1

HCID 58274179Methyl 2-(4-diethylaminophenyl)-6-hydroxy-2-phenyl-2H-naphtho[1,2-b]pyran-5-carboxylateYield 56%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl 1,4-dihydroxynaphthalene-2-carboxylate (4.00 g, 18.3 mmol), 1-(4-diethylaminophenyl)-1-phenyl-prop-2-yn-1-ol (4.67 g, 18.3 mmol) and Al2O3 (4.5 g) in toluene (150 mL) was refluxed for 3 hrs, filtered whilst hot and the solvent removed under reduced pressure. The residue was filtered through a short plug of silica using DCM (20% hexane) as eluent followed by a second filtration through silica using DCM as eluent. The residue was crystallised from acetone-MeOH and the product isolated as a yellow solid (4.89 g, 56%)

Workup

  1. filtrationfiltered whilst hot and the solvent
  2. customremoved under reduced pressure
  3. filtrationThe residue was filtered through a short plug of silica
  4. filtrationfollowed by a second filtration through silica
  5. customThe residue was crystallised from acetone-MeOH

Sources & evidence

ORD record
ord-f61d7ba87f3949c183152061a7762a4c
Source dataset
uspto-grants-2014_04
Patent number
US08703978B2

Reaction notes

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