Toluene → HCID 68485517, compound

HRID 72257Notes

Reaction equation

HRID 72257 reaction equation
C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([CH3:21])=[C:18]([Pb+3])[CH:19]=1.[CH:22]12[CH2:29][CH:26]([CH2:27][CH2:28]1)[C:25](=[O:30])[CH2:24][C:23]2=[O:31].C1(C)C=CC=CC=1>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([CH3:21])=[C:18]([CH:24]2[C:25](=[O:30])[CH:26]3[CH2:29][CH:22]([CH2:28][CH2:27]3)[C:23]2=[O:31])[CH:19]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 144686Bicyclo(3.2.1)octane-2,4-dioneHCID 178476526[Diacetyloxy-(5-chloro-2-methylphenyl)plumbyl] acetate

Product 1

HCID 68485517HCID 68485517, compoundYield 33.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 5-chloro-2-methylphenyllead triacetate (0.41 g, 0.80 mmol) in chloroform (4 ml) is added bicyclo[3.2.1]octane-2,4-dione (0.10 g, 0.72 mmol) and 4-dimethylaminopyridine (0.46 g, 3.62 mmol), and the reaction mixture is stirred at room temperature for 5 minutes. Next toluene (1 ml) is added, and the mixture is stirred at 80° C. for 1 hour (pre-heated oil bath). The reaction mixture is allowed to cool to room temperature, quenched with 1M hydrochloric acid, and the organic phase separated. The aqueous phase is further washed with dichloromethane (×2), and again the phases are separated. All organics are combined then evaporated under reduced pressure to give a crude oil. Purification by preparative reverse-phase HPLC furnishes 3-(5-chloro-2-methylphenyl)bicyclo[3.2.1]octane-2,4-dione (0.063 g, 33%) as a colourless gum.

Workup

  1. stirringthe mixture is stirred at 80° C. for 1 hour
  2. temperature(pre-heated oil bath)
  3. temperatureto cool to room temperature
  4. customquenched with 1M hydrochloric acid
  5. customthe organic phase separated
  6. washThe aqueous phase is further washed with dichloromethane (×2)
  7. customagain the phases are separated
  8. customAll organics are combined then evaporated under reduced pressure
  9. customto give a crude oil
  10. customPurification by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-52e14d12fcc5455ea0366d1449ee46b8
Source dataset
uspto-grants-2014_09
Patent number
US08828908B2

Reaction notes

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