Ethyl Acetate → HCID 86634715, compound

HRID 910893Notes

Reaction equation

HRID 910893 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[H-].[Na+].[Cl:14][C:15]1[CH:20]=[C:19]([N+]([O-])=O)[CH:18]=[CH:17][N:16]=1.C(OCC)(=O)C>CN(C=O)C>[Cl:14][C:15]1[CH:20]=[C:19]([O:1][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH:18]=[CH:17][N:16]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 88068Methyl 3-HydroxybenzoateHCID 7351522-Chloro-4-nitropyridine

Product 1

HCID 86634715HCID 86634715, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3-hydroxybenzoate (2.88 g, 18.9 mmol) was added to a mixture of 60% sodium hydride in mineral oil (0.757 g, 18.9 mmol) in DMF (20 mL). The reaction mixture was stirred for 20 minutes and then cooled in an ice bath. 2-Chloro-4-nitropyridine (3.00 g, 18.9 mmol) was added and the reaction mixture was stirred for 1 hour at 0° C., and then overnight at room temperature. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed twice with water and brine, dried, and concentrated. The residue was purified by MPLC (Biotage) eluting with 5:1 hexane:ethyl acetate to afford methyl 3-(2-chloropyridin-4-yloxy)benzoate (4.49 g, 90.0% yield) as a thick oil. 1H NMR (CDCl3) δ 8.26 (d, 1H), 7.98 (d, 1H), 7.77 (s, 1H), 7.54 (t, 1H), 7-31 (d, 1H), 6.82 (s, 1H), 6.79 (d, 1H).

Workup

  1. temperaturecooled in an ice bath
  2. stirringthe reaction mixture was stirred for 1 hour at 0° C.
  3. customovernight
  4. customat room temperature
  5. customThe reaction mixture was partitioned between water and ethyl acetate
  6. washThe organic layer was washed twice with water and brine
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified by MPLC (Biotage)
  10. washeluting with 5:1 hexane

Sources & evidence

ORD record
ord-2d524a531bc849a5803247cf73395c0f
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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