Ethyl Acetate → HCID 18755528, compound

HRID 1838636Notes

Reaction equation

HRID 1838636 reaction equation
C(Cl)(=O)C([Cl:4])=O.[OH:7][C:8]1[C:13]([CH3:15])([CH3:14])[C:12](=[O:16])[C:11]([CH3:18])([CH3:17])[C:10](=[O:19])[C:9]=1[C:20]([C:22]1[C:23]([CH3:32])=[N:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=1)=O.ClC1C(C)(C)C(=O)C(C)(C)C(=O)C=1C(C1C(C)=NC(C(F)(F)F)=CC=1)=O.C(OCC)(=O)C>ClCCl.CN(C)C=O.CCCCCC>[Cl:4][C:20]([C:22]1[C:23]([CH3:32])=[N:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=1)=[C:9]1[C:8](=[O:7])[C:13]([CH3:15])([CH3:14])[C:12](=[O:16])[C:11]([CH3:18])([CH3:17])[C:10]1=[O:19]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 65578Oxalyl chlorideHCID 11383649HCID 11383649, compoundHCID 178432829HCID 178432829, compound

Product 1

HCID 18755528HCID 18755528, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

7.0 g (55 mmol) of oxalyl chloride are introduced into 18.5 g (50 mmol) of 5-hydroxy-2,2,6,6-tetramethyl-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohex-4-ene-1,3-dione (compound A2-B354), dissolved in 50 ml of dichloromethane; 5 drops of dimethylformamide are added, and the mixture is slowly heated up to boiling point. After approximately 30 minutes, after the evolution of gas has ceased, the mixture is evaporated and the product is crystallized by adding n-hexane. The main product obtained is pure 5-chloro-2,2,6,6-tetramethyl-4-(2-methyl-6-trifluoromethylpyridine3-carbonyl)cyclohex-4-ene-1,3dione, m.p. 119.5-120° C. Further HPLC-separation of the mother liquor using 5-10% ethyl acetate in hexane gives the isomer 6-[chloro-(2-methyl-6-trifluoromethylpyridine-3-yl)methylene]-2,2,4,4-tetramethylcyclohexane-1,3,5-trione, m.p. 92.5-93° C.

Workup

  1. temperaturethe mixture is slowly heated up
  2. customthe mixture is evaporated
  3. customthe product is crystallized
  4. additionby adding n-hexane
  5. customThe main product obtained

Sources & evidence

ORD record
ord-468e77d3fc884b1099978f9d85f820dd
Source dataset
uspto-grants-2004_01
Patent number
US06673938B1

Reaction notes

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