Hydrochloric Acid → HCID 69725509, compound

HRID 278403Notes

Reaction equation

HRID 278403 reaction equation
[CH2:1]([C:5]1[O:9][N:8]=[C:7]([CH3:10])[CH:6]=1)[C:2]([CH3:4])=[O:3].[CH3:11][C:12]1[O:17][C:16](=[O:18])[CH2:15][CH2:14][CH:13]=1.C(=O)([O-])[O-].Cl>C(#N)C>[CH3:10][C:7]1[CH:6]=[C:5]([CH2:1][C:2](=[O:3])[CH2:4][C:16](=[O:18])[CH2:15][CH2:14][CH2:13][C:12](=[O:17])[CH3:11])[O:9][N:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 19660Carbonate IonHCID 1380343,4-Dihydro-6-methyl-2H-pyran-2-oneHCID 11789279HCID 11789279, compound

Product 1

HCID 69725509HCID 69725509, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.39 g of 5-acetonyl-3-methylisoxazole, 1.68 g of 3,4-dihydro-6-methyl-2H-pyran-2-one and 3.42 g of cecium carbonate were added to 20 ml of acetonitrile to heat at reflux for 3 hours. After returning to room temperatrure, the reaction solution was poured into 100 ml of ice water with hydrochloric acid added, and extracted with ethyl acetate. The organic layer was washed with water and then with saturated salt water, and dried over magnesium sulfate. The solvent was concentrated under reduced pressure. The obtained crude product was purified on silica gel column chromatography to give 2.03 g of the title compound as a colorless viscous liquid.

Workup

  1. temperatureto heat
  2. temperatureat reflux for 3 hours
  3. additionadded
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialwith saturated salt water, and dried over magnesium sulfate
  7. concentrationThe solvent was concentrated under reduced pressure
  8. customThe obtained crude product
  9. customwas purified on silica gel column chromatography

Sources & evidence

ORD record
ord-a597d167768949509dc3517ccd024bb7
Source dataset
uspto-grants-2002_03
Patent number
US06359143B1

Reaction notes

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