Hexane → HCID 22404779, compound

HRID 440702Notes

Reaction equation

HRID 440702 reaction equation
[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][C:10]([CH3:13])([CH3:12])[O:11][C:6]=2[C:5]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]([CH3:25])[C:15]2=[O:26])=[C:4]([F:27])[CH:3]=1.S(OOS([O-])(=O)=O)([O-])(=O)=[O:29].[K+].[K+].C(OCC)(=O)C.CCCCCC>C(#N)C.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[Cl:1][C:2]1[C:7]2[C:8](=[O:29])[CH2:9][C:10]([CH3:13])([CH3:12])[O:11][C:6]=2[C:5]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:22])[F:23])[N:16]([CH3:25])[C:15]2=[O:26])=[C:4]([F:27])[CH:3]=1

Participants

8

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 24412Potassium PersulfateHCID 22404729HCID 22404729, compound

Product 1

HCID 22404779HCID 22404779, compoundYield 47.5%

Reagents, catalysts & solvents 3

HCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

By the method of Example 3, Step A, 1.8 grams (0.004 mole) of 3-(5-chloro-3,4-dihydro-2,2-dimethyl-7-fluoro-2H-1-benzopyran-8-yl)-1-methyl-6-trifluoromethyluracil was reacted with 3.5 grams (0.013 mole) of potassium persulfate and 1.1 grams (0.004 mole) of copper(II) sulfate pentahydrate in 30 mL of acetonitrile and 30 mL of water. The crude reaction mixture was subjected to column chromatography on silica gel, with 1:4 ethyl acetate:hexane as the eluant. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.8 gram of 3-(5-chloro-3,4-dihydro-2,2-dimethyl-7-fluoro-2H-1-benzopyran-4-on-8-yl)-1-methyl-6-trifluoromethyluracil. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThe crude reaction mixture
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cba5941ed1044377a5df9d0be550a1d0
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

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