Butyryl chloride → HCID 118228953, compound

HRID 629127Notes

Reaction equation

HRID 629127 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[O:5][C:4](=[O:10])[CH:3]=1.[C:11](Cl)(=[O:15])[CH2:12][CH2:13][CH3:14]>FC(F)(F)C(O)=O>[C:11]([C:3]1[C:4](=[O:10])[O:5][C:6]([CH2:8][CH3:9])=[CH:7][C:2]=1[OH:1])(=[O:15])[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 8855Butyryl chlorideHCID 547135586-Ethyl-4-hydroxy-2H-pyran-2-one

Product 1

HCID 118228953HCID 118228953, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
90 °C

Procedure

According to the method of Douglas and Money (see: Can. J. Chem. 1968, 46, 695), 4-hydroxy-6-ethyl-2-pyrone (see: Hsung, et. al. Synthesis 2007, 749; 1.24 g, 8.85 mmol) was dissolved in trifluoroacetic acid (4 mL) in a pressure-safe vessel. Butyryl chloride (1.0 mL, 9.73 mmol) was added and the solution flushed with argon. The vessel was sealed and stirred in a 90° C. heating bath overnight. After cooling to room temperature, the solution was poured onto powdered sodium bicarbonate (9 g) before water (80 mL) was added carefully. Organics were extracted from the aqueous slurry with dichloromethane (3×80 mL), dried with magnesium sulfate, filtered, and concentrated. The crude product was purified by chromatography on silica gel with gradient elution (10→20% ether in hexanes) to afford 3-butyryl-6-ethyl-4-hydroxy-2-pyrone (1.20 g, 65%) as an oily solid. Used without further characterization.

Workup

  1. customthe solution flushed with argon
  2. customThe vessel was sealed
  3. temperatureheating bath overnight
  4. temperatureAfter cooling to room temperature
  5. additionthe solution was poured
  6. additionwas added carefully
  7. extractionOrganics were extracted from the aqueous slurry with dichloromethane (3×80 mL)
  8. dry with materialdried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product was purified by chromatography on silica gel with gradient elution (10→20% ether in hexanes)

Sources & evidence

ORD record
ord-035e07a7f0db46889748e5f7de6bcacd
Source dataset
uspto-grants-2016_04
Patent number
US09315495B2

Reaction notes

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