Hydrochloric Acid → HCID 91080937, compound

HRID 43319Notes

Reaction equation

HRID 43319 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH:7]2[CH2:12][C:11](=[O:13])[CH2:10][C:9](=[O:14])[CH2:8]2)[CH2:3][CH2:2]1.C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[CH3:34][C:35]1[C:40]([Pb+3])=[C:39]([CH3:42])[CH:38]=[C:37]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:36]=1.Cl>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[CH3:34][C:35]1[C:40]([CH:10]2[C:11](=[O:13])[CH2:12][CH:7]([CH:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)[CH2:8][C:9]2=[O:14])=[C:39]([CH3:42])[CH:38]=[C:37]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:36]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 189213635-(Tetrahydro-2H-pyran-4-YL)cyclohexane-1,3-dioneHCID 178476522HCID 178476522, compound

Product 1

HCID 91080937HCID 91080937, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent2×

Procedure

To a mixture of 5-(tetrahydropyran-4-yl)cyclohexane-1,3-dione (196 mg; 1 mmol) and 4-dimethylaminopyridine (610 mg; 5 mmol) is added dry chloroform (4 ml) under an atmosphere of nitrogen, 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 a solution of 3,5-dimethylbiphen-4-yllead triacetate (1.2 mmol) in chloroform. The reaction mixture is heated under reflux for 1 hour. The reaction mixture is cooled to room temperature, acidified to pH 1 with 2N aqueous hydrochloric acid, filtered and the filtrate is extracted with dichloromethane (2×40 ml). The organic extracts are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated in vacuo. The residue is purified by column chromatography on silica gel to give 2-(3,5-dimethylbiphen-4-yl)-5-(tetrahydropyran-4-yl)cyclohexane-1,3-dione.

Workup

  1. dissolutionare dissolved
  2. temperatureThe reaction mixture is heated
  3. temperatureunder reflux for 1 hour
  4. temperatureThe reaction mixture is cooled to room temperature
  5. filtrationfiltered
  6. extractionthe filtrate is extracted with dichloromethane (2×40 ml)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe filtrate is evaporated in vacuo
  10. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ab0ad6a964094714b12416aad178ce3c
Source dataset
uspto-grants-2013_09
Patent number
US08536351B2

Reaction notes

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