4-(5-Phenyl-2-thienyl)-2-naphthol → 3-(2-Fluorophenyl)-6-(5-phenyl-2-thienyl)-3-(4-pyrrolidinophenyl)-3H-naphtho[2,1-b]pyran

HRID 2369645Notes

Reaction equation

HRID 2369645 reaction equation
[C:1]1([C:7]2[S:11][C:10]([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:15]=[C:14]([OH:22])[CH:13]=3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]([C:34]1[CH:39]=[CH:38][C:37]([N:40]2[CH2:44][CH2:43][CH2:42][CH2:41]2)=[CH:36][CH:35]=1)(O)[C:31]#[CH:32]>C1(C)C=CC=CC=1>[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]1([C:34]2[CH:35]=[CH:36][C:37]([N:40]3[CH2:44][CH2:43][CH2:42][CH2:41]3)=[CH:38][CH:39]=2)[O:22][C:14]2[CH:13]=[C:12]([C:10]3[S:11][C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:8][CH:9]=3)[C:21]3[C:16]([C:15]=2[CH:32]=[CH:31]1)=[CH:17][CH:18]=[CH:19][CH:20]=3

Participants

4

Reactant 2

HCID 582741834-(5-Phenyl-2-thienyl)-2-naphtholHCID 866536111-(2-Fluorophenyl)-1-(4-pyrrolidinophenyl)prop-2-yn-1-ol

Product 1

HCID 582741753-(2-Fluorophenyl)-6-(5-phenyl-2-thienyl)-3-(4-pyrrolidinophenyl)-3H-naphtho[2,1-b]pyran

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 4-(5-phenyl-2-thienyl)-2-naphthol, (0.52 g, 1.73 mmol) and 1-(2-fluorophenyl)-1-(4-pyrrolidinophenyl)prop-2-yn-1-ol (0.51 g, 1.73 mmol) in toluene (50 ml) was warmed to 50° C. Acidic Al2O3 (1 g) was then added and the mixture heated to reflux for 1.5 h. After cooling, the solution was filtered, washed with hot toluene (100 ml) and the solvent removed. The resulting residue was then flash chromatographed eluting with EtOAc-hexane (1:9). The fractions were combined and the solvent removed. After precipitation from acetone-MeOH, the title compound (0.52 g, 52%) was collected as dark green crystals.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 1.5 h
  3. temperatureAfter cooling
  4. filtrationthe solution was filtered
  5. washwashed with hot toluene (100 ml)
  6. customthe solvent removed
  7. customflash chromatographed
  8. washeluting with EtOAc-hexane (1:9)
  9. customthe solvent removed
  10. customAfter precipitation from acetone-MeOH
  11. customthe title compound (0.52 g, 52%) was collected as dark green crystals

Sources & evidence

ORD record
ord-a98a1ca61cee42bf95f6953d0ae13e47
Source dataset
uspto-grants-2014_04
Patent number
US08703978B2

Reaction notes

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