p-Toluenesulfonic acid → 3-(4-fluorophenyl)-6-(4'-hydroxybiphen-4-yl)-3-phenyl-3H-naphtho[2,1-b]pyran

HRID 2090516Notes

Reaction equation

HRID 2090516 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([OH:11])[C:9]#[CH:10])=[CH:4][CH:3]=1.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21](S(O)(=O)=O)=[CH:20][CH:19]=1.[C:29](=[O:32])(O)[O-].[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[O:11][C:20]3[CH:19]=[C:18]([C:28]4[CH:3]=[CH:4][C:5]([C:8]5[CH:12]=[CH:13][C:29]([OH:32])=[CH:10][CH:9]=5)=[CH:6][CH:7]=4)[C:23]4[C:22]([C:21]=3[CH:10]=[CH:9]2)=[CH:17][CH:16]=[CH:15][CH:14]=4)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 125491061-(4-Fluorophenyl)-1-phenyl-2-propyn-1-ol

Product 1

HCID 591887153-(4-fluorophenyl)-6-(4'-hydroxybiphen-4-yl)-3-phenyl-3H-naphtho[2,1-b]pyran

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-(4′-hydroxy-4-biphenyl)-2-naphthol (16.14 g, 52 mmol), 1-(4-fluorophenyl)-1-phenylprop-2-yn-1-ol (11.7 g, 52 mmol) and toluene-4-sulphonic acid (0.05 g) in toluene (200 mL) was heated at reflux. After 2 h the mixture was poured into saturated sodium bicarbonate solution (400 mL), extracted with dichloromethane (DCM) (4×100 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was chromatographed on silica using EtOAc (10-30% in hexanes) to afford 3-(4-fluorophenyl)-6-(4′-hydroxybiphen-4-yl)-3-phenyl-3H-naphtho[2,1-b]pyran which was collected, the solvent removed under reduced pressure, the residue was filtered through a short plug of silica using DCM as eluent and the solvent removed under reduced pressure to give the title compound (19.37 g, 72%) as an orange solid which was used without further purification.

Workup

  1. temperatureat reflux
  2. extractionextracted with dichloromethane (DCM) (4×100 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed under reduced pressure
  5. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-30aaf40921f14168844a6f897e998c7c
Source dataset
uspto-grants-2013_05
Patent number
US08436184B2

Reaction notes

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