Phosphorus pentachloride → HCID 59562418, compound

HRID 1849963Notes

Reaction equation

HRID 1849963 reaction equation
[CH3:1][C:2]1([CH3:12])[C:7](=O)[CH2:6][C:5](=[O:9])[C:4]([CH3:11])([CH3:10])[O:3]1.P(Cl)(Cl)(Cl)(Cl)[Cl:14]>C(Cl)(Cl)Cl>[Cl:14][C:7]1[C:2]([CH3:12])([CH3:1])[O:3][C:4]([CH3:11])([CH3:10])[C:5](=[O:9])[CH:6]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 199092752,2,6,6-Tetramethyloxane-3,5-dione

Product 1

HCID 59562418HCID 59562418, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 2,2,6,6-tetramethylpyran-3,5-dione (741 mg, 4.35 mmol) in chloroform (10 ml) is added phosphorus pentachloride (454 mg, 2.18 mmol), and the reaction is heated to reflux for 5 hours. Silica gel is added to the cooled crude reaction mixture, the solvent is evaporated under reduced pressure and the residue is purified by flash chromatography on silica gel to give 5-chloro-2,2,6,6-tetramethyl-6H-pyran-3-one (349 mg).

Workup

  1. temperaturethe reaction is heated
  2. temperatureto reflux for 5 hours
  3. additionSilica gel is added to the
  4. temperaturecooled crude
  5. customreaction mixture
  6. customthe solvent is evaporated under reduced pressure
  7. customthe residue is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-f61b8ff3e7654fb6984ee2af1c5da5c0
Source dataset
uspto-grants-2015_02
Patent number
US08956999B2

Reaction notes

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