Pyridine → alpha-[Acetoxy(5-norbornen-2-yl)methyl]-gamma-butyrolactone

HRID 431415

Reaktionsgleichung

Reaktionsgleichung von HRID 431415
N1C=CC=CC=1.[OH:7][CH:8]([CH:15]1[CH2:20][CH:19]2[CH2:21][CH:16]1[CH:17]=[CH:18]2)[CH:9]1[CH2:14][CH2:13][O:12][C:10]1=[O:11].[C:22](OC(=O)C)(=[O:24])[CH3:23]>CN(C)C1C=CN=CC=1.O>[C:22]([O:7][CH:8]([CH:15]1[CH2:20][CH:19]2[CH2:21][CH:16]1[CH:17]=[CH:18]2)[CH:9]1[CH2:14][CH2:13][O:12][C:10]1=[O:11])(=[O:24])[CH3:23]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 183456893-[(Bicyclo[2.2.1]hept-5-en-2-yl)(hydroxy)methyl]oxolan-2-one2×

Produkt 1

HCID 18761072alpha-[Acetoxy(5-norbornen-2-yl)methyl]-gamma-butyrolactoneAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

To 127 g of pyridine were added 208 g of α-[hydroxy(5-norbornen-2-yl)methyl]-γ-butyrolactone (Monomer 1), 123 g of acetic anhydride and 6 g of 4-dimethylaminopyridine. Reaction was effected at 25° C. for 10 hours. Water, 30 g, was added to the reaction mixture to stop reaction, followed by hexane extraction. The organic layer was washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuum. Purification by silica gel column chromatography yielded 245 g (yield 98%) of α-[acetoxy(5-norbornen-2-yl)methyl]-γ-butyrolactone.

Aufarbeitung

  1. customReaction
  2. customreaction
  3. extractionfollowed by hexane extraction
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum
  8. customPurification by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-77154b4f71174c1f8296e946b2bfb9b2
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660448B2

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