Pyridine → 6-(4-tert.-Butylbenzoyl)-5-(4-fluorophenyl)-7-isopropylspiro[chromen-2,1'-cyclobutan]-4(3H)-one

HRID 1516721Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1516721
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.ClCCl.N1C=CC=CC=1.[C:32]([C:36]1[CH:41]=[CH:40][C:39]([CH:42]([OH:67])[C:43]2[C:44]([C:60]3[CH:65]=[CH:64][C:63]([F:66])=[CH:62][CH:61]=3)=[C:45]3[C:53](=[CH:54][C:55]=2[CH:56]([CH3:58])[CH3:57])[O:52][C:48]2([CH2:51][CH2:50][CH2:49]2)[CH2:47][C:46]3=[O:59])=[CH:38][CH:37]=1)([CH3:35])([CH3:34])[CH3:33]>C(OCC)(=O)C.[OH-].[Na+]>[C:32]([C:36]1[CH:37]=[CH:38][C:39]([C:42]([C:43]2[C:44]([C:60]3[CH:65]=[CH:64][C:63]([F:66])=[CH:62][CH:61]=3)=[C:45]3[C:53](=[CH:54][C:55]=2[CH:56]([CH3:58])[CH3:57])[O:52][C:48]2([CH2:51][CH2:50][CH2:49]2)[CH2:47][C:46]3=[O:59])=[O:67])=[CH:40][CH:41]=1)([CH3:34])([CH3:35])[CH3:33]

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 6344Dichloromethane2×HCID 159087TriacetoxyperiodinaneHCID 580029576-[(4-tert-Butylphenyl)(hydroxy)methyl]-5-(4-fluorophenyl)-7-isopropylspiro[chromen-2,1'-cyclo-butan]-4(3H)-one

Produkt 1

HCID 580029326-(4-tert.-Butylbenzoyl)-5-(4-fluorophenyl)-7-isopropylspiro[chromen-2,1'-cyclobutan]-4(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

91 mg (0.21 mmol) of 1,1-dihydro-1,1,1-triacetoxy-1,2-benziodoxol-3(1H)-one are dissolved in 1.4 ml of abs. dichloromethane and cooled to −30° C. 12 μl (0.14 mmol) of pyridine are added, followed by the dropwise addition of 68 mg (0.14 mmol) of 6-[(4-tert-butylphenyl)(hydroxy)-methyl]-5-(4-fluorophenyl)-7-isopropylspiro[chromen-2,1′-cyclobutan]-4(3H)-one (Example 55A), dissolved in 0.6 ml of abs. dichloromethane. The mixture is slowly warmed to 0° C. and stirred at this temperature for 1.5 h. The mixture is diluted with ethyl acetate, 5 ml of 1 N aqueous sodium hydroxide solution are added and the mixture is then extracted twice with ethyl acetate. The combined organic phases are washed once with 1 N hydrochloric acid and twice with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The crude product is dried under high vacuum and then reacted without further purification. This gives 81 mg (>100% of theory) of the title compound.

Aufarbeitung

  1. dissolutiondissolved in 0.6 ml of abs
  2. additionare added
  3. extractionthe mixture is then extracted twice with ethyl acetate
  4. washThe combined organic phases are washed once with 1 N hydrochloric acid and twice with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dry with materialThe crude product is dried under high vacuum
  9. customreacted without further purification

Quellen und Nachweise

ORD-Eintrag
ord-65b3d722f4904f18b72ca52ccbb1f71c
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08227511B2

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