Acetic Acid → HCID 178467260, compound

HRID 1700630Notes

Reaction equation

HRID 1700630 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]1[CH2:12][C:11](=[O:13])[CH2:10][C:9](=[O:14])[CH2:8]1.[C:15](O)(=[O:17])[CH3:16].CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]1[CH2:12][C:11](=[O:13])[C:10](=[C:15]([OH:17])[CH3:16])[C:9](=[O:14])[CH2:8]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 18317511HCID 18317511, compound

Product 1

HCID 178467260HCID 178467260, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(3-chlorothiophen-2-yl)cyclohexane-1,3-dione (2.0 g), acetic acid (0.90 g) and dimethylaminopyridine (1.6 g) in dimethylformamide (100 ml) was added dicyclohexylcarbodiimide (2.3 g), and the mixture was stirred at room temperature for 13 hours. Under reduced pressure, the solvent was evaporated, and to the residue was ethyl acetate. The mixture was washed with potassium hydrogensulfate solution and water, and to the mixture was added 1N sodium hydroxide solution. The aqueous layer was washed with diethylether and neutralized with 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure to give oil of 5-(3-chlorothiophen-2-yl)-2-(1-hydroxyethylidene)-cyclohexane-1,3-dione (2.2 g).

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. washThe mixture was washed with potassium hydrogensulfate solution and water
  3. additionto the mixture was added 1N sodium hydroxide solution
  4. washThe aqueous layer was washed with diethylether and neutralized with 1N hydrochloric acid
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried with magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-575e538602ec4f64971edfa402d7a796
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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