Dicyclohexylcarbodiimide → 5-(2-Chlorophenyl)-2-(1-hydroxy-2-methoxyethylidene)cyclohexane-1,3-dione

HRID 1700684Notes

Reaction equation

HRID 1700684 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][C:12](=[O:14])[CH2:11][C:10](=[O:15])[CH2:9]1.[CH3:16][O:17][CH2:18][C:19](O)=[O:20].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][C:12](=[O:14])[C:11](=[C:19]([OH:20])[CH2:18][O:17][CH3:16])[C:10](=[O:15])[CH2:9]1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 12251Methoxyacetic AcidHCID 8753605-(2-Chlorophenyl)cyclohexane-1,3-dione

Product 1

HCID 183177735-(2-Chlorophenyl)-2-(1-hydroxy-2-methoxyethylidene)cyclohexane-1,3-dioneYield 65%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(2-chlorophenyl)cyclohexane-1,3-dione (1.0 g), 4-dimethylaminopyridine (0.82 g) and methoxyacetic acid (0.73 g) in dimethylformamide (40 ml) was added dicyclohexylcarbodiimide (1.0 g), and the mixture was stirred at room temperature for 3 days. Under reduced pressure, the solvent was evaporated, and to the residue was added ethyl acetate. Insoluble materials were filtered off, and the organic layer was extracted with 1N sodium hydroxide solution. To the aqueous layer was added 1N hydrochloric acid to make the solution acidic, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give 5-(2-chlorophenyl)-2-(1-hydroxy-2-methoxyethylidene)cyclohexane-1,3-dione (0.86 g) as oil.

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. additionto the residue was added ethyl acetate
  3. filtrationInsoluble materials were filtered off
  4. extractionthe organic layer was extracted with 1N sodium hydroxide solution
  5. additionTo the aqueous layer was added 1N hydrochloric acid
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water and saturated brine
  8. dry with materialdried with magnesium sulfate
  9. customUnder reduced pressure, the solvent was evaporated

Sources & evidence

ORD record
ord-81f3cde5e2724d20ae3d3f75728b8139
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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