Acetic Acid → HCID 53730400, compound

HRID 1600621Notes

Reaction equation

HRID 1600621 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2]([O:4]CC)=O.[CH3:11][C:12]1[C:17]([N+:18]([O-:20])=[O:19])=[C:16]([N:21]([CH3:31])[CH2:22][CH2:23][O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)[CH:15]=[CH:14][C:13]=1[C:32]([F:35])([F:34])[F:33].[O-]CC.[K+].C(O)(=O)C>O1CCCC1.O>[CH3:31][N:21]([C:16]1[C:17]([N+:18]([O-:20])=[O:19])=[C:12]([CH2:11][C:2](=[O:4])[C:1]([O:8][CH2:9][CH3:10])=[O:7])[C:13]([C:32]([F:34])([F:35])[F:33])=[CH:14][CH:15]=1)[CH2:22][CH2:23][O:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][O:26]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7268Diethyl OxalateHCID 21714329HCID 21714329, compoundHCID 23670592Potassium ethoxide

Product 1

HCID 53730400HCID 53730400, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Diethyl oxalate (1.94 g, 13.2 mmol) and then a solution of 2-methyl-4-[N-methyl-N-[2-(2-tetrahydro-2H-pyranyl)oxyethyl]amino]-3-nitrobenzotrifluoride (2.40 g, 6.62 mmol) in tetrahydrofuran (40 ml) were added dropwise to a mixture of potassium ethoxide (1.11 g, 13.2 mmol) and tetrahydrofuran (60 ml) at room temperature. The reaction mixture was stirred at room temperature for 6 hours and then cooled to 3° C., and acetic acid (1.59 g, 26.5 mmol) was added dropwise. The reaction mixture thus obtained was poured into cold water and extracted twice with ethyl acetate. The extract solution was washed with a 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/9) to obtain an oil of ethyl [3-[N-methyl-N-[2-(2-tetrahydro-2H-pyranyl)oxyethyl]-amino]-2-nitro-6-trifluoromethylphenyl]pyruvate.

Workup

  1. temperaturecooled to 3° C.
  2. customThe reaction mixture thus obtained
  3. extractionextracted twice with ethyl acetate
  4. washThe extract solution was washed with a 5% aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/9)

Sources & evidence

ORD record
ord-3e1bc6f021e04db1a5b5862f74ec22df
Source dataset
uspto-grants-1999_11
Patent number
US05977100

Reaction notes

Loading…