Triethylamine → 1-Pyridine-4-yl-2-m-tolyl-ethane-1,2-dione

HRID 566718Notes

Reaction equation

HRID 566718 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[N:14]1[CH:19]=[CH:18][C:17]([CH:20]([OH:30])[CH:21]([C:23]2[CH:24]=[C:25]([CH3:29])[CH:26]=[CH:27][CH:28]=2)[OH:22])=[CH:16][CH:15]=1.C(N(CC)CC)C>C(Cl)Cl>[N:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:30])[C:21]([C:23]2[CH:24]=[C:25]([CH3:29])[CH:26]=[CH:27][CH:28]=2)=[O:22])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 212664901-Pyridine-4-yl-2-m-tolyl-ethane-1,2-diol

Product 1

HCID 212665371-Pyridine-4-yl-2-m-tolyl-ethane-1,2-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Dimethylsufoxide (2.85 mL, 40 mmole) was dropwise added into a solution of trifluoroacetic anhydride (4.24 mL, 30 mmole) in methylene chloride (100 mL) at 78° C. The reaction mixture was stirred at that temperature for 10 min before the addition of 1-pyridine-4-yl-2-m-tolyl-ethane-1,2-diol (2.29 g, 10 mmole) in methylene chloride (50 mL). The mixture was stirred additional 1 hr at that temperature. Finally, the mixture was quenched with triethylamine (8.5 mL, 60 mmole) and the resulting mixture was allowed to warmed to r.t. The reaction was diluted with methylene chloride, washed with NH4Cl and brine, dried with MgSO4, evaporated, and finally, purified through a silica column (ethyl acetate/hexane) to give the title compound. MS (m/z): Calcd. C14H11NO2(M+): 225, found (M+H)+: 226.1.

Workup

  1. washwashed with NH4Cl and brine
  2. dry with materialdried with MgSO4
  3. customevaporated
  4. customfinally, purified through a silica column (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b92efcb2166644d090698d547e7f88f1
Source dataset
uspto-grants-2001_01
Patent number
US06174901B1

Reaction notes

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