4-Methylbenzyl alcohol → HCID 23725536, compound

HRID 2219428Notes

Reaction equation

HRID 2219428 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][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][OH:35])=[CH:32][CH:31]=1>CN(C=O)C>[CH3:13][C:12]1[O:11][N:10]=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]=1[C:6]1[N:7]=[C:3]([CH2:2][O:35][CH2:34][C:33]2[CH:36]=[CH:37][C:30]([CH3:29])=[CH:31][CH:32]=2)[N:4]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 115054-Methylbenzyl alcoholHCID 23725534HCID 23725534, compound

Product 1

HCID 23725536HCID 23725536, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

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 DMF (0.5 mL) was added to a suspension on NaH (55% in oil, 5.5 mg, 0.13 mmol) in DMF (0.5 mL) containing 4-methylbenzyl alcohol (15.5 mg, 0.13 mmol) in DMF (0.5 mL) and the resulting mixture stirred at room temperature for 2 h. The mixture was then poured onto water and extracted with ethyl acetate. The combined organic layers were then washed with brine and water and then dried over sodium sulphate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 80:20) afforded the title compound (11.6 mg, 19%) which was obtained as a yellow gum. MS: m/e=481.3 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-c4ca76b84e7647278b2b6e80c8e0b39f
Source dataset
uspto-grants-2008_08
Patent number
US07414061B2

Reaction notes

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