Phosphorus pentachloride → HCID 68568880, compound

HRID 41667Notes

Reaction equation

HRID 41667 reaction equation
[CH3:1][C:2]12[O:11][CH:8]([CH2:9][CH2:10]1)[CH:7]1[CH:3]2[C:4](=[O:13])[CH2:5][C:6]1=O.P(Cl)(Cl)(Cl)(Cl)[Cl:15]>C(Cl)(Cl)Cl>[Cl:15][C:6]1[CH:7]2[CH:3]([C:2]3([CH3:1])[O:11][CH:8]2[CH2:9][CH2:10]3)[C:4](=[O:13])[CH:5]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 685648701-Methyl-10-oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione

Product 1

HCID 68568880HCID 68568880, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1-methyl-10-oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione (3 g, 16.6 mmol) in chloroform (8 ml) is added PCl5 portionwise. The reaction mixture is stirred and heated at reflux for 5 hours. The reaction mixture is evaporated to dryness The crude product is purified by flash chromatography on silica gel to give 5-chloro-1-methyl-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (1.39 g).

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. customThe reaction mixture is evaporated to dryness The crude product
  4. customis purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-d4c209656121418b9e37ee965c078d8b
Source dataset
uspto-grants-2013_09
Patent number
US08530667B2

Reaction notes

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