Hydrochloric Acid → 3-(4-fluorophenyl)-6-(4'-(hexanoyloxy)biphen-4-yl)-3-phenyl-3H-naphtho[2,1-b]pyran

HRID 2090519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2090519
[C:1](Cl)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[O:21][C:20]3[CH:22]=[C:23]([C:30]4[CH:35]=[CH:34][C:33]([C:36]5[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=5)=[CH:32][CH:31]=4)[C:24]4[C:29]([C:19]=3[CH:18]=[CH:17]2)=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:12][CH:11]=1.N1C=CC=CC=1.Cl>C(Cl)Cl>[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[O:21][C:20]3[CH:22]=[C:23]([C:30]4[CH:35]=[CH:34][C:33]([C:36]5[CH:41]=[CH:40][C:39]([O:42][C:1](=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:38][CH:37]=5)=[CH:32][CH:31]=4)[C:24]4[C:29]([C:19]=3[CH:18]=[CH:17]2)=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:12][CH:11]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 67340Hexanoyl chloride2×HCID 591887153-(4-fluorophenyl)-6-(4'-hydroxybiphen-4-yl)-3-phenyl-3H-naphtho[2,1-b]pyran

Produkt 1

HCID 591887093-(4-fluorophenyl)-6-(4'-(hexanoyloxy)biphen-4-yl)-3-phenyl-3H-naphtho[2,1-b]pyranAusbeute 72,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Hexanoyl chloride (5.01 g, 37 mmol) was added dropwise to a solution of 3-(4-fluorophenyl)-6-(4′-hydroxybiphen-4-yl)-3-phenyl-3H-naphtho[2,1-b]pyran (19.37 g, 37 mmol) in DCM (100 mL) containing pyridine (20 mL) at 0° C. After ½ h additional hexanoyl chloride (5.01 g, 37 mmol) was added. Stirring was continued for a further ½ h more, the solution was poured into HCl (2 M, 400 mL), separated and extracted with DCM (2×100 mL), the combined organic phases were washed with water saturated sodium bicarbonate (200 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was filtered through a short plug of silica using DCM (50% in hexanes) as eluent. The solvent was removed under reduced and the residue triturated alternately with hexanes and methanol twice. The residue was dried under vacuum to give the title compound (16.51 g, 72%) as a yellow foam, mp 64-65° C.

Aufarbeitung

  1. customseparated
  2. extractionextracted with DCM (2×100 mL)
  3. washthe combined organic phases were washed with water saturated sodium bicarbonate (200 mL)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure
  6. filtrationThe residue was filtered through a short plug of silica
  7. customThe solvent was removed
  8. customthe residue triturated alternately with hexanes and methanol twice
  9. customThe residue was dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-eadfda23f1194b3a93e05f3a44c3dc95
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436184B2

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