Allyl Alcohol → HCID 13769420, compound

HRID 1382146Notes

Reaction equation

HRID 1382146 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([Cl:15])[C:12]([N:16]2[C:20](=[O:21])[N:19]([CH:22]([F:24])[F:23])[C:18]([CH3:25])=[N:17]2)=[CH:11][C:3]=1[O:4][CH:5]([CH3:10])[C:6]([O:8][CH3:9])=[O:7].C[O-].[Na+].[CH2:29](O)[CH:30]=C>C(OCC)C>[Cl:1][C:2]1[CH:14]=[C:13]([Cl:15])[C:12]([N:16]2[C:20](=[O:21])[N:19]([CH:22]([F:24])[F:23])[C:18]([CH3:25])=[N:17]2)=[CH:11][C:3]=1[O:4][CH:5]([CH3:10])[C:6]([O:8][CH2:9][CH:29]=[CH2:30])=[O:7]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 10942334Sodium MethoxideHCID 14392488HCID 14392488, compound2×

Product 1

HCID 13769420HCID 13769420, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Under a dry nitrogen atmosphere, a stirred solution of 0.5 g (0.0013 mole) of methyl 2-[2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]propionate (Compound 2) and approximately 0.01 g of sodium methoxide in 30 mL of 2-propen-1-ol was heated at reflux. After approximately 5 mL of methanol was collected in a Dean-Stark trap, the reaction mixture was cooled slightly, and the remaining solvent removed by distillation under reduced pressure leaving a residue. This residue was dissolved in diethyl ether and washed with water. The organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 0.55 g of 2-propenyl 2-[2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]propionate as an oil, Compound B2.

Workup

  1. temperatureat reflux
  2. customAfter approximately 5 mL of methanol was collected in a Dean-Stark trap
  3. temperaturethe reaction mixture was cooled slightly
  4. customthe remaining solvent removed by distillation under reduced pressure
  5. customleaving a residue
  6. washwashed with water
  7. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1b27ec33fa9143ee9ce1aae6ff8427f4
Source dataset
uspto-grants-1989_02
Patent number
US04806145

Reaction notes

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