(E)-1,3-Dichloropropene → (E)-2-(1-Methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methyl-6-(3-chloroprop-2-enyloxy)pyridine

HRID 366297Notes

Reaction equation

HRID 366297 reaction equation
[OH:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[N:13]([CH3:14])[N:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[CH:5]=[C:4]([CH3:19])[CH:3]=1.[H-].[Na+].[Cl:22]/[CH:23]=[CH:24]/[CH2:25]Cl>C(#N)C.CN(C=O)C.CCCCC.C(OCC)(=O)C>[CH3:14][N:13]1[C:9]([O:8][C:6]2[CH:5]=[C:4]([CH3:19])[CH:3]=[C:2]([O:1][CH2:25]/[CH:24]=[CH:23]/[Cl:22])[N:7]=2)=[CH:10][C:11]([C:15]([F:18])([F:17])[F:16])=[N:12]1

Participants

7

Reactant 3

HCID 24726(E)-1,3-DichloropropeneHCID 24758Sodium hydride2×HCID 178429419HCID 178429419, compound

Product 1

HCID 15477174(E)-2-(1-Methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methyl-6-(3-chloroprop-2-enyloxy)pyridineYield 52.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 22335286Ethyl acetate pentaneSolvent

Procedure

A mixture of 6-hydroxy-2-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methylpyridine (0.9 g, 3.3 mmol) and NaH (60 % in oil, 0.16 g, 4 mmol) in acetonitrile (20 ml) and DMF (1 ml) is stirred for 10 min at ambient temperature and (E)-1,3-dichloropropene (0.4 g, 3.6 mmol) is added. After stirring for 60 h at ambient temperature, the remaining NaH is deactivated and the resulting mixture is diluted with pentane/ethyl acetate (by volume ration 1/1) and filtered through a bed of silica gel. The filtrate is washed with water. The organic layer is dried with anhydrous magnesium sulfate, filtered and evaporated in vacuo. Purification by flash chromatography (silica gel: pentane/ethyl acetate 9/1 v/v) yields the title compound (0.6 g, 52 % yield) as an colorless oil.

Workup

  1. stirringAfter stirring for 60 h at ambient temperature
  2. filtrationfiltered through a bed of silica gel
  3. washThe filtrate is washed with water
  4. dry with materialThe organic layer is dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customPurification by flash chromatography (silica gel: pentane/ethyl acetate 9/1 v/v)

Sources & evidence

ORD record
ord-34dd5c0c7f8a40b59706a99c17232257
Source dataset
uspto-grants-2000_10
Patent number
US06130188

Reaction notes

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