Ethyl Acetate → ethyl 2-methyl-2-(methylsulfonyl)-4-(4-phenyl-1H-imidazol-1-yl)butanoate

HRID 2405951Notes

Reaction equation

HRID 2405951 reaction equation
[CH3:1][S:2]([CH:5]([CH3:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:4])=[O:3].I[CH2:13][CH2:14][N:15]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:17]=[CH:16]1.C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>CN(C=O)C>[CH3:11][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])([CH2:13][CH2:14][N:15]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:17]=[CH:16]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 10511577Ethyl 2-(methylsulfonyl)propanoateHCID 867102511-(2-iodoethyl)-4-phenyl-1H-imidazole

Product 1

HCID 70818083ethyl 2-methyl-2-(methylsulfonyl)-4-(4-phenyl-1H-imidazol-1-yl)butanoateYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Ethyl 2-(methylsulfonyl)propanoate (377 mg, 2.09 mmol, 1 eq) and 1-(2-iodoethyl)-4-phenyl-1H-imidazole (623 mg, 2.09 mmol, 1 eq) in DMF (7 mL) was added Cs2CO3(1.70 g, 5.22 mmol, 2.5 eq) and the reaction mixture was allowed to stir overnight at RT, then for a further 24 h at 45° C. EtOAc was added and the mixture was washed with water. The organic layer was dried over MgSO4, filtered and concentrated. The crude product mixture was purified by flash chromatography on silica gel eluting with 10-95% ethyl acetate in heptanes to give ethyl 2-methyl-2-(methylsulfonyl)-4-(4-phenyl-1H-imidazol-1-yl)butanoate (335 mg, 46% yield). LC-MS M+H+351.1.

Workup

  1. waitfor a further 24 h at 45° C
  2. washthe mixture was washed with water
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product mixture was purified by flash chromatography on silica gel eluting with 10-95% ethyl acetate in heptanes

Sources & evidence

ORD record
ord-ed6f2ebd72684f4f9eab2a47f1fbbc4c
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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