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

HRID 431415

Reaction equation

HRID 431415 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-77154b4f71174c1f8296e946b2bfb9b2
Source dataset
uspto-grants-2003_12
Patent number
US06660448B2

Linked notes

Loading…