Methanol → HCID 59321526, compound

HRID 2423494Notes

Reaction equation

HRID 2423494 reaction equation
C[O-].[Na+].CO.[C:6]([CH2:11][C:12]([O:14][CH3:15])=[O:13])(=[O:10])[CH:7]([CH3:9])[CH3:8].O[N:17]=[C:18](Cl)[C:19]1[C:20]([CH3:26])=[N:21][CH:22]=[CH:23][C:24]=1[CH3:25]>C1COCC1>[CH3:26][C:20]1[C:19]([C:18]2[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:6]([CH:7]([CH3:9])[CH3:8])[O:10][N:17]=2)=[C:24]([CH3:25])[CH:23]=[CH:22][N:21]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 2759969Methyl 4-methyl-3-oxopentanoateHCID 10942334Sodium MethoxideHCID 86619861HCID 86619861, compound

Product 1

HCID 59321526HCID 59321526, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 0.5 N solution of sodium methoxide in methanol (2.8 mL, 1.4 mmol) was added to a solution of methyl isobutyrylacetate (0.19 mL, 1.34 mmol) in THF (0.24 mL) at 0° C. A solution of the crude N-hydroxy-2,4-dimethyl-3-pyridinecarboximidoyl chloride (0.22 g, 1.2 mmol) in THF (2.2 mL) was added and the resulting mixture was allowed to warm to room temperature and stir overnight. The solution was concentrated and the residue was partitioned between ethyl acetate and brine. The organic layer was dried with MgSO4, filtered and concentrated. The residue was chromatographed (silica gel, hexane to 3:2 ethyl acetate:hexane) to provide methyl 3-(2,4-dimethyl-3-pyridinyl)-5-(1-methylethyl)-4-isoxazolecarboxylate (0.17 g, 52%). ESI-LCMS m/z 275 (M+H)+.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was partitioned between ethyl acetate and brine
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed (silica gel, hexane to 3:2 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-ba6ab3b65bcb4a25b84196a512e6af7c
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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