Hydrochloric Acid → (1RS,2SR,6RS,7SR)-4-(3,5-dimethylbiphen-4-yl)-10-oxa-tricyclo[5.2.1.02,6]decane-3,5-dione

HRID 1430755Notes

Reaction equation

HRID 1430755 reaction equation
[CH:1]12[O:10][CH:7]([CH2:8][CH2:9]1)[CH:6]1[CH:2]2[C:3](=[O:12])[CH2:4][C:5]1=[O:11].C(Cl)(Cl)Cl.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[CH3:29][C:30]1[C:35]([Pb+3])=[C:34]([CH3:37])[CH:33]=[C:32]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:31]=1.Cl>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[CH3:29][C:30]1[C:35]([CH:4]2[C:3](=[O:12])[CH:2]3[CH:6]([CH:7]4[O:10][CH:1]3[CH2:9][CH2:8]4)[C:5]2=[O:11])=[C:34]([CH3:37])[CH:33]=[C:32]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:31]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 5935195110-Oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dioneHCID 178476522HCID 178476522, compound

Product 1

HCID 67777251(1RS,2SR,6RS,7SR)-4-(3,5-dimethylbiphen-4-yl)-10-oxa-tricyclo[5.2.1.02,6]decane-3,5-dione

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of (1RS,2SR,6RS,7SR)-10-oxatricyclo[5.2.1.02,6]decane-3,5-dione (166 mg, 1 mmol) and 4-dimethylaminopyridine (610 mg, 5 mmol) under an atmosphere of nitrogen is added dry chloroform (5.6 ml), and the mixture is stirred at room temperature until all the solids are dissolved. To this solution is then added dry toluene (2 ml), and 3,5-dimethylbiphen-4-yllead triacetate (0.5 M solution in dry chloroform, 2.4 ml, 1.2 mmol). The reaction mixture is heated at reflux for 1 hour, then cooled to room temperature, acidified to pH1 with 2N aqueous hydrochloric acid, filtered and extracted with dichloromethane. The organic extracts are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under reduced pressure. The crude product is purified by column chromatography on silica gel to give (1RS,2SR,6RS,7SR)-4-(3,5-dimethylbiphen-4-yl)-10-oxa-tricyclo[5.2.1.02,6]decane-3,5-dione.

Workup

  1. dissolutionare dissolved
  2. temperatureThe reaction mixture is heated
  3. temperatureat reflux for 1 hour
  4. temperaturecooled to room temperature
  5. filtrationfiltered
  6. extractionextracted with dichloromethane
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe filtrate evaporated under reduced pressure
  10. customThe crude product is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a4648e85d6d94be588e55164e6e9a00f
Source dataset
uspto-grants-2015_01
Patent number
US08940913B2

Reaction notes

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