Dimethyl Sulfoxide → Ethyl 7-(4-(2-methyl-1h-imidazol-1-yl)phenyl)-4,7-dioxoheptanoate

HRID 2280320Notes

Reaction equation

HRID 2280320 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[CH2:9][CH2:10][C:11](=[O:19])[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][CH:3]=1.[CH3:21][C:22]1[NH:23][CH:24]=[CH:25][N:26]=1.CS(C)=O>O>[CH3:21][C:22]1[N:23]([C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:20])[CH2:9][CH2:10][C:11](=[O:19])[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][CH:3]=2)[CH:24]=[CH:25][N:26]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 127492-MethylimidazoleHCID 10564686Ethyl 4-fluoro-gamma,zeta-dioxobenzeneheptanoate

Product 1

HCID 58305778Ethyl 7-(4-(2-methyl-1h-imidazol-1-yl)phenyl)-4,7-dioxoheptanoateYield 27.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

Ethyl 7-(4-fluorophenyl)-4,7-dioxoheptanoate (2.00 g, 7.1 mmol) and 2-methyl-1H-imidazole (7.0 g, 86 mmol) were taken up into DMSO (4 mL). The mixture was heated to 180° C. under microwave for 72 min. Water (100 mL) was added and the mixture was extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with brine (40 mL), dried over Na2SO4, filtered, concentrated and purified by silica gel column chromatography (DCM to DCM:MeOH=25:1) to afford the title compound as a dark brown solid (660 mg, yield 25%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (50 mL×3)
  2. washThe combined organic layers were washed with brine (40 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (DCM to DCM:MeOH=25:1)

Sources & evidence

ORD record
ord-34713e7318834dad939436c5a101e6ce
Source dataset
uspto-grants-2015_09
Patent number
US09138427B2

Reaction notes

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