Toluene → Methyl 6-hydroxy-3-phenyl-3-(4-pyrrolidinophenyl)-2H-naphtho[1,2-b]pyran-5-carboxylate

HRID 2369640Notes

Reaction equation

HRID 2369640 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].[C:17]1([C:23]([C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:29][CH:28]=2)(O)[C:24]#C)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:38]1(C)C=CC=CC=1>>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]2[O:12][CH2:38][C:23]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)([C:27]3[CH:32]=[CH:31][C:30]([N:33]4[CH2:34][CH2:35][CH2:36][CH2:37]4)=[CH:29][CH:28]=3)[CH:24]=[C:4]2[C:3]=1[C:13]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 3

HCID 1140TolueneHCID 604167Methyl 1,4-dihydroxy-2-naphthoateHCID 224637731-Phenyl-1-(4-pyrrolidinophenyl)prop-2-yn-1-ol

Product 1

HCID 67162696Methyl 6-hydroxy-3-phenyl-3-(4-pyrrolidinophenyl)-2H-naphtho[1,2-b]pyran-5-carboxylateYield 62%

Procedure

A mixture of methyl 1,4-dihydroxynaphthalene-2-carboxylate (3.93 g, 18 mmol), 1-phenyl-1-(4-pyrrolidinophenyl)prop-2-yn-1-ol (5 g, 18 mmol) and Al2O3 (4 g) in PhMe (100 mL) was heated at reflux for 1.5 h, cooled, filtered, the residue washed with DCM and the solvent removed under reduced pressure. The residue was filtered through a short plug of silica using DCM (40% in hexanes) as eluent. The solvent was removed under reduced pressure and the residue was crystallized from Et2O-hexanes to give the title compound (5.47 g, 62%) as a yellow powder.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 h
  3. temperaturecooled
  4. filtrationfiltered
  5. washthe residue washed with DCM
  6. customthe solvent removed under reduced pressure
  7. filtrationThe residue was filtered through a short plug of silica
  8. customThe solvent was removed under reduced pressure
  9. customthe residue was crystallized from Et2O-hexanes

Sources & evidence

ORD record
ord-6533723d9d4b447a8c28f2642b7273b5
Source dataset
uspto-grants-2014_04
Patent number
US08703978B2

Reaction notes

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