Phosphorus oxychloride → HCID 86691197, compound

HRID 1470555Notes

Reaction equation

HRID 1470555 reaction equation
[CH2:1]([O:3][C:4](=[O:24])/[CH:5]=[CH:6]/[C:7]1[CH:8]=[CH:9][C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[N+:11]([O-])[CH:12]=1)[CH3:2].O=P(Cl)(Cl)[Cl:27]>>[Cl:27][C:12]1[C:7](/[CH:6]=[CH:5]/[C:4]([O:3][CH2:1][CH3:2])=[O:24])=[CH:8][CH:9]=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[N:11]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 66714742HCID 66714742, compound

Product 1

HCID 86691197HCID 86691197, compoundYield 67%

Procedure

A solution of (E)-5-(3-ethoxy-3-oxoprop-1-enyl)-2-(3-(trifluoromethyl)phenyl)pyridine 1-oxide (9 g, 26.7 mmol) in POCl3 (45 mL) was stirred at 80° C. for 5 h. After completion, reaction mixture was poured into ice water (150 mL), extracted with EtOAc (2×100 mL), combined extracts were treated with NaHCO3 solution, washed with water (100 mL), brine (100 mL), dried over anhydrous Na2SO4, filtered and evaporated. The crude residue was purified by column chromatography by using (SiO2) EtOAc:Pet ether (2:98) to afford (E)-ethyl 3-(2-chloro-6-(3-(trifluoromethyl)phenyl)pyridin-3-yl)acrylate (6.3 g, 67%) as yellow solid.

Workup

  1. customAfter completion, reaction mixture
  2. extractionextracted with EtOAc (2×100 mL)
  3. additionwere treated with NaHCO3 solution
  4. washwashed with water (100 mL), brine (100 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-54864d9ff5c94676b596161e2665e74f
Source dataset
uspto-grants-2015_04
Patent number
US09006449B2

Reaction notes

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