Dimethylformamide → HCID 21491883, compound

HRID 1973507Notes

Reaction equation

HRID 1973507 reaction equation
P(Cl)(Cl)([Cl:3])=O.CN(C)C=O.[O:11]=[C:12]1[CH2:17][C:16](=O)[CH2:15][CH:14]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[CH:13]1[C:26]([O:28][CH2:29][CH3:30])=[O:27].C([O-])([O-])=O.[Na+].[Na+]>ClCCl>[Cl:3][C:16]1[CH2:15][CH:14]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[CH:13]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:12](=[O:11])[CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 20239929HCID 20239929, compound

Product 1

HCID 21491883HCID 21491883, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of phosphoryl chloride (3.53 g.) and dimethylformamide (1.68 g.) at 0° C was added a cooled solution of ethyl 2,4-dioxo-6-p-tolylcyclohexanecarboxylate (6.2 g.) a dione of formula II prepared as in Example 1, in dichloromethane (60 ml.). After keeping at 0° C for 30 minutes the mixture was poured into excess 2N-Na2CO3 solution and extracted with ether. After washing the ether extracts with water and drying over magnesium sulphate, evaporation of the solvents gave crude ethyl 4-chloro-2-oxo-6-p-tolyl-3-cyclohexenecarboxylate (a halide of formula IV) as a pale yellow oil.

Workup

  1. extractionextracted with ether
  2. washAfter washing the ether
  3. dry with materialdrying over magnesium sulphate, evaporation of the solvents

Sources & evidence

ORD record
ord-2d67e25d87a2461ba3abaec4fd07ef98
Source dataset
uspto-grants-1976_12
Patent number
US03997590

Reaction notes

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