Ethyl trifluoromethanesulphonate → 1-(1-Ethyl-2-methyl-1H-imidazol-5-yl)ethan-1-one

HRID 1064330Notes

Reaction equation

HRID 1064330 reaction equation
[O:1]([CH2:9][CH3:10])S(C(F)(F)F)(=O)=O.[C:11]1([C:17](C2C=CC=CC=2)(C2C=CC=CC=2)[N:18]2[CH:22]=[C:21](C(=O)C)[N:20]=[C:19]2[CH3:26])C=CC=CC=1>C(Cl)Cl>[CH2:17]([N:18]1[C:22]([C:9](=[O:1])[CH3:10])=[CH:21][N:20]=[C:19]1[CH3:26])[CH3:11]

Participants

4

Reactant 2

HCID 67924Ethyl trifluoromethanesulphonateHCID 22273469HCID 22273469, compound

Product 1

HCID 222734751-(1-Ethyl-2-methyl-1H-imidazol-5-yl)ethan-1-oneYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethyl triflate (11 ml, 83.2 mmol) was added dropwise over 15 minutes to a solution of 1-(triphenylmethyl)-2-methyl-4-acetylimidazole (Method 34; 23.4 g, 64 mmol) in DCM (300 ml) and the mixture stirred for 5 hours at ambient temperature. The solution was diluted with DCM (100 ml) and extracted with 1M aqueous citric acid solution (5×75 ml). The aqueous extracts were combined, basified with solid sodium hydrogen carbonate and the extracted with DCM (5×75 ml). The organic extracts were combined, dried and evaporated to give the title compound (8.59 g, 88%) as a pale yellow oil. NMR 1.32 (t, 3H), 2.41 (s, 6H), 4.29 (q, 2H), 7.68 (s, 1H); m/z 153.

Workup

  1. extractionextracted with 1M aqueous citric acid solution (5×75 ml)
  2. extractionthe extracted with DCM (5×75 ml)
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-64ce71c66512486abddb8e34131c19c0
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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