Pyridine → 3-Hydroxy-5,5-dimethyl-4-[4-(methylsulfonyl)phenyl]-2(5H)-furanone

HRID 376347

Reaktionsgleichung

Reaktionsgleichung von HRID 376347
[OH:1][C:2]([CH3:16])([CH3:15])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1)=O.N1C=CC=CC=1.C([O:26][CH2:27][C:28](Cl)=[O:29])(=O)C.C1CCN2C(=NCCC2)CC1>CC#N.CCOC(C)=O.O.[Cl-].[Na+].O.C(Cl)Cl.C1(C)C=CC=CC=1>[CH3:15][C:2]1([CH3:16])[O:1][C:27](=[O:26])[C:28]([OH:29])=[C:3]1[C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1

Komponenten

10

Edukt 4

HCID 1049PyridineHCID 26297Acetoxyacetyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 154285142-Hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)propan-1-one

Produkt 1

HCID 155422043-Hydroxy-5,5-dimethyl-4-[4-(methylsulfonyl)phenyl]-2(5H)-furanoneAusbeute 42,9 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 21877217Toluene methylene chlorideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a 0° C. solution of the alcohol of Example 1, Step 3 (14.0 g, 57.8 mmol) in CH3CN (180 mL) were added pyridine (10.0 mL) and acetoxyacetyl chloride (12.7 g, 93.0 mmol) after a period of 7 h at r.t., DBU (15.0 mL) was added to the reaction mixture. After a period of 1 h at 80° C., a second portion of DBU (20.0 mL) was added. The reaction mixture was kept at 80° C. for 18 h. The reaction mixture allowed to cool to r.t. The mixture was diluted with EtOAc (500 mL) and H2O (500 mL) and acidified with 6NHCl. After the addition of brine (100 mL), the aqueous phase was extracted 2 times with EtOAc. The organic phase was evaporated to provide a brown residue. To the solid was added a 2:1 mixture of CH2Cl2 -toluene (150 mL). The solid was filtered and washed with CH2Cl2 -toluene to provide 7.0 g of the title compound.

Aufarbeitung

  1. waitThe reaction mixture was kept at 80° C. for 18 h
  2. extractionthe aqueous phase was extracted 2 times with EtOAc
  3. customThe organic phase was evaporated
  4. customto provide a brown residue
  5. additionTo the solid was added
  6. filtrationThe solid was filtered
  7. washwashed with CH2Cl2 -toluene

Quellen und Nachweise

ORD-Eintrag
ord-e4b5878b53194adaa89a59d653b767ae
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06020343

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