Pyridine → HCID 86587552, compound

HRID 1282416Notes

Reaction equation

HRID 1282416 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C:12]#[C:13][C:14]([CH2:18][F:19])([OH:17])[CH2:15][F:16].N1C=CC=CC=1>C(=O)([O-])[O-].[Ba+2].[Pd+2].C(=O)([O-])[O-].C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1/[CH:12]=[CH:13]\[C:14]([CH2:18][F:19])([OH:17])[CH2:15][F:16]

Participants

5

Reactant 2

HCID 1049PyridineHCID 18424411HCID 18424411, compound

Product 1

HCID 86587552HCID 86587552, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 16211661HCID 16211661, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(2-chloro-5-trifluoromethylphenyl)-1-fluoro-2-fluoromethyl-3-butyn-2-ol (44.5 g), 5% palladium-barium carbonate (6.6 g), pyridine (2.3 g) and ethyl acetate (500 ml) was stirred under a hydrogen atmosphere at room temperature for 10 days. The catalyst was filtered off from the reaction mixture; subsequent concentrating under reduced pressure gave 4-(2-chloro-5-trifluoromethylphenyl)-1-fluoro-2-fluoromethyl-3-cis-buten-2-ol (44.0 g).

Workup

  1. filtrationThe catalyst was filtered off from the reaction mixture
  2. concentrationsubsequent concentrating under reduced pressure

Sources & evidence

ORD record
ord-e0a8cddc3cfa4decb04239ffeaf8e0e3
Source dataset
uspto-grants-2002_09
Patent number
US06455708B1

Reaction notes

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