Sodium Methoxide → HCID 18973830, compound

HRID 2395055Notes

Reaction equation

HRID 2395055 reaction equation
[CH2:1]([O:8][C:9]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:10]=1[CH2:11][CH2:12][C:13]1[N:18]=[C:17](Cl)[C:16]([C:20]([O:22][CH3:23])=[O:21])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][O-:30].[Na+]>CO>[CH2:1]([O:8][C:9]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:10]=1[CH2:11][CH2:12][C:13]1[N:18]=[C:17]([O:30][CH3:29])[C:16]([C:20]([O:22][CH3:23])=[O:21])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18974085HCID 18974085, compound

Product 1

HCID 18973830HCID 18973830, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of methyl 6-[2-benzyloxy-5-bromophenethyl]-2-chloro-3-pyridinecarboxylate (7.0 g) and sodium methoxide (2.5 mole equivalents) in methanol was heated at 140° C. for 5 hours in a Carius Tube. The solvent was evaporated and the residue extracted with ethyl acetate and washed with saturated aqueous NH4Cl, water and brine. The organic solution was dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography on 7734 silica gel, eluting with 1% MeOH/CH2Cl2, to give methyl 6-[2-benzyloxy-5-bromophenethyl]-2-methoxy-3-pyridinecarboxylate (6.16 g).

Workup

  1. customThe solvent was evaporated
  2. extractionthe residue extracted with ethyl acetate
  3. washwashed with saturated aqueous NH4Cl, water and brine
  4. dry with materialThe organic solution was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography on 7734 silica gel
  8. washeluting with 1% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-0fc48c76c171495ca8d35152401ae67e
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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