Phosphorus pentachloride → HCID 59562500, compound

HRID 1849972Notes

Reaction equation

HRID 1849972 reaction equation
[CH3:1][C:2]12[O:9][CH:6]([CH2:7][CH2:8]1)[C:5](=O)[CH2:4][C:3]2=[O:11].P(Cl)(Cl)(Cl)(Cl)[Cl:13]>C(Cl)(Cl)Cl>[Cl:13][C:5]1[CH:6]2[O:9][C:2]([CH3:1])([CH2:8][CH2:7]2)[C:3](=[O:11])[CH:4]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 67524030HCID 67524030, compound

Product 1

HCID 59562500HCID 59562500, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1-methyl-8-oxa-bicyclo[3.2.1]octane-2,4-dione (175 mg, 1.14 mmol) in chloroform (2 ml) is added, under N2, in one portion, the phosphorous pentachloride (135 mg, 0.65 mmol). The reaction mixture is stirred for 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 4-chloro-1-methyl-8-oxa-bicyclo[3.2.1]oct-3-en-2-one (93 mg).

Workup

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

Sources & evidence

ORD record
ord-f973f5cfddb34566a345528007034731
Source dataset
uspto-grants-2015_02
Patent number
US08956999B2

Reaction notes

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