Phosphorus oxychloride → Isohexane ethyl acetate

HRID 2207650Notes

Reaction equation

HRID 2207650 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([F:19])=[C:8]([C:10]2[CH:15]=[CH:14][N+:13]([O-])=[C:12]([C:17]#[N:18])[CH:11]=2)[CH:9]=1)[CH3:2].P(Cl)(Cl)([Cl:22])=[O:21]>>[C:4]([O:3][CH2:1][CH3:2])(=[O:21])[CH3:5].[CH3:5][CH2:6][CH2:7][CH:8]([CH3:10])[CH3:9].[Cl:22][C:14]1[N:13]=[C:12]([C:17]#[N:18])[CH:11]=[C:10]([C:8]2[CH:9]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=[CH:6][C:7]=2[F:19])[CH:15]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 89649701HCID 89649701, compound

Product 2

HCID 21882781Isohexane ethyl acetateHCID 89648832HCID 89648832, compound

Procedure

A mixture of 4-(5-ethoxy-2-fluoro-phenyl)-1-oxido-pyridin-1-ium-2-carbonitrile (which may be prepared as described in Description 112) (5.1 g, 19.75 mmol) in phosphorus oxychloride (50 mL) was heated to reflux under nitrogen for 2 hrs. The POCl3 was evaporated and toluene was added and then evaporated. Ethyl acetate and satd. aq. NaHCO3 were added and the product was extracted into ethyl acetate (3×200 ml). The extracts were dried (Na2SO4) and concentrated. Chromatography (silica gel, ethyl acetate/isohexane) on this crude material gave 6-chloro-4-(5-ethoxy-2-fluoro-phenyl)pyridine-2-carbonitrile (D113) as a white solid;

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for 2 hrs
  3. customThe POCl3 was evaporated
  4. additiontoluene was added
  5. customevaporated
  6. additionaq. NaHCO3 were added
  7. extractionthe product was extracted into ethyl acetate (3×200 ml)
  8. dry with materialThe extracts were dried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b52559b3468543a79d4e95c7bae98085
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

Loading…