Sodium Methoxide → HCID 67422152, compound

HRID 2219425Notes

Reaction equation

HRID 2219425 reaction equation
Cl[CH2:2][C:3]1[N:4]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)[CH:5]=[C:6]([C:8]2[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:10][O:11][C:12]=2[CH3:13])[N:7]=1.[CH3:29][O-:30].[Na+]>CO>[CH3:29][O:30][CH2:2][C:3]1[N:4]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)[CH:5]=[C:6]([C:8]2[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:10][O:11][C:12]=2[CH3:13])[N:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 23725534HCID 23725534, compound

Product 1

HCID 67422152HCID 67422152, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[2-chloromethyl-1-(4-nitro-phenyl)-1H-imidazol-4-yl]-5-methyl-3-phenyl-isoxazole (50 mg, 0.13 mmol) in methanol (1 mL) was added a solution of sodium methoxide (5.4 M in MeOH, 23.5 μL, 0.13 mmol) and the resulting mixture stirred at room temperature overnight. The mixture was then poured onto water and extracted with ethyl acetate. The combined organic layers were then dried over sodium sulphate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 80:20) afforded the title compound (27 mg, 55%) which was obtained as a yellow solid. MS: m/e=391.1 [M+H]+.

Workup

  1. additionThe mixture was then poured onto water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were then dried over sodium sulphate
  4. customevaporated
  5. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 80:20)

Sources & evidence

ORD record
ord-7bbc6cba13d94b21a8d2cc5cfc3e4f7d
Source dataset
uspto-grants-2008_08
Patent number
US07414061B2

Reaction notes

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