Chloroform → 2-(4'-Chloro-4-ethylbiphen-3-yl)-4,4-dimethyl-1,3-cyclohexanedione

HRID 400376Notes

Reaction equation

HRID 400376 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][C:3]1=[O:9].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Cl:23][C:24]1[CH:38]=[CH:37][C:27]([C:28]2[CH:29]=[CH:30][C:31]([CH2:35][CH3:36])=[C:32]([Pb+3])[CH:33]=2)=[CH:26][CH:25]=1.CN(C1C=CC=CN=1)C.C(Cl)(Cl)Cl>ClCCl.Cl.C1(C)C=CC=CC=1>[Cl:23][C:24]1[CH:38]=[CH:37][C:27]([C:28]2[CH:33]=[CH:32][C:31]([CH2:35][CH3:36])=[C:30]([CH:4]3[C:3](=[O:9])[C:2]([CH3:10])([CH3:1])[CH2:7][CH2:6][C:5]3=[O:8])[CH:29]=2)=[CH:26][CH:25]=1

Participants

8

Reactant 4

HCID 6212ChloroformHCID 218852-DimethylaminopyridineHCID 1363601,3-Cyclohexanedione, 4,4-dimethyl-HCID 178476534HCID 178476534, compound

Product 1

HCID 1233116992-(4'-Chloro-4-ethylbiphen-3-yl)-4,4-dimethyl-1,3-cyclohexanedione

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 4,4-dimethyl-1,3-cyclohexanedione (0.21 g, 1.5 mmol), 4′-chloro-4-ethylbiphen-3-yllead triacetate (1.0 g, 1.7 mmol) and dimethylaminopyridine (0.93 g, 7.6 mmol) is added anhydrous chloroform (11 ml) and anhydrous toluene (2.8 ml). The reaction mixture is heated at 80° C. for 4 hours and then cooled to room temperature. The mixture is diluted with dichloromethane (50 ml) and 2M aqueous hydrochloric acid (50 ml) and filtered through diatomaceous earth. The filtrate is partitioned, the aqueous layer is extracted with dichloromethane (50 ml) and the organic extracts are combined, washed with 2M aqueous hydrochloric acid (50 ml), brine (50 ml), dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The crude product is purified by preparative reverse phase HPLC to give 2-(4′-chloro-4-ethylbiphen-3-yl)-4,4-dimethyl-1,3-cyclohexanedione.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through diatomaceous earth
  3. customThe filtrate is partitioned
  4. extractionthe aqueous layer is extracted with dichloromethane (50 ml)
  5. washwashed with 2M aqueous hydrochloric acid (50 ml), brine (50 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate is evaporated under reduced pressure
  9. customThe crude product is purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-6f64732888e84335a023bf0dc1b3dde4
Source dataset
uspto-grants-2014_06
Patent number
US08741806B2

Reaction notes

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