Water → HCID 22161757, compound

HRID 1088717Notes

Reaction equation

HRID 1088717 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[C:10](/[CH:15]=[CH:16]/[C:17](OC)=[O:18])=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC.C(OCC)(=O)C>[C:1]1([CH2:7][O:8][C:9]2[C:10]([CH2:15][CH2:16][CH2:17][OH:18])=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22161738(E)-Methyl 3-[3-(phenylmethoxy)pyridin-2-yl]-2-propenoate

Product 1

HCID 22161757HCID 22161757, compoundYield 12.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (E)-methyl 3-[3-(phenylmethoxy)-2-pyridinyl]-2-propenoate (12.0 g) in dry ether (100 ml) was added to a stirred suspension of lithium aluminium hydride (5 g) in ether (200 ml) under nitrogen. The mixture was heated at reflux overnight and treated successively with water (5 ml), 2N sodium hydroxide (10 ml) and water (100 ml). Ethyl acetate (250 ml) was added and the mixture was filtered. The solution was washed with water and brine, dried and concentrated to an oil which was purified by FCC eluting with cyclohexane/ethyl acetate/triethylamine (80:20:1) followed by ethyl acetate/triethylamine (99:1) to give the title compound as a pale orange oil (1.4 g), t.l.c. (ethyl acetate/triethylamine 99:1) Rf 0.21.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. filtrationthe mixture was filtered
  4. washThe solution was washed with water and brine
  5. customdried
  6. concentrationconcentrated to an oil which
  7. customwas purified by FCC
  8. washeluting with cyclohexane/ethyl acetate/triethylamine (80:20:1)

Sources & evidence

ORD record
ord-5a49b458d42f4fc38b203447691a3dcf
Source dataset
uspto-grants-1990_10
Patent number
US04963564

Reaction notes

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