Sodium Methoxide → HCID 22036484, compound

HRID 493347Notes

Reaction equation

HRID 493347 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.[CH3:12][O-:13].[Na+]>O1CCOCC1>[CH3:12][O:13][C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 22036297HCID 22036297, compound

Product 1

HCID 22036484HCID 22036484, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of the product of Example 203, Step 1(513 mg, 2.96 mmol) and freshly prepared NaOMe (3.06 g, 56.6 mmol) in dry dioxane (25 mL) was heated in a sealed Pyrex tube at 130° C. for 24 h. The solvent was evaporated under reduced pressure and the residue was dissolved in CH2Cl2. The organic phase was washed with brine, dried (MgSO4), and concentrated to give the crude product as an oil (430 mg). Purification by column chromatography, using isohexane/EtOAc (1:1) as an eluent, gave the title product as a white solid. Yield 258 mg (51%); MS m/z 169 (M)+. Anal. (C8H11NO3) C, H, N.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto give the crude product as an oil (430 mg)
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-0389b9185fb843ff88be037d11e2f79d
Source dataset
uspto-grants-2009_05
Patent number
US07534794B2

Reaction notes

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