Ethyl Acetate → Methyl 3-methoxy-2-[2-(2-isopropoxy-6-trifluoromethylpyrimidin-4-yloxymethyl) phenyl]acrylate

HRID 991173Notes

Reaction equation

HRID 991173 reaction equation
[K].[CH:2]([O:5][C:6]1[N:11]=[C:10]([OH:12])[CH:9]=[C:8]([C:13]([F:16])([F:15])[F:14])[N:7]=1)([CH3:4])[CH3:3].[CH3:17][O:18][CH:19]=[C:20]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31]Br)[C:21]([O:23][CH3:24])=[O:22].C(OCC)(=O)C>CCCCCCCC>[CH3:17][O:18][CH:19]=[C:20]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31][O:12][C:10]1[CH:9]=[C:8]([C:13]([F:15])([F:16])[F:14])[N:7]=[C:6]([O:5][CH:2]([CH3:4])[CH3:3])[N:11]=1)[C:21]([O:23][CH3:24])=[O:22]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 5462222PotassiumHCID 53395349Methyl 2-[2-(bromomethyl)phenyl]-3-methoxyprop-2-enoateHCID 178458952HCID 178458952, compound

Product 1

HCID 53395020Methyl 3-methoxy-2-[2-(2-isopropoxy-6-trifluoromethylpyrimidin-4-yloxymethyl) phenyl]acrylate

Reagents, catalysts & solvents 1

HCID 356OctaneSolvent2×

Procedure

3.04 g of potassium salt of 2-isopropoxy-6-trifluoromethyl-4-hydroxypyrimidine and 3.65 g of methyl 3-methoxy-2-(2-bromomethylphenyl)acrylate were suspended in 50 ml of octane. The resulting suspension was reacted at reflux of octane for 5 hours and cooled down to room temperature. 30 ml of ethyl acetate was added and insoluble matter was filtrated. The precipitate separated by filtration was washed with 20 ml of etyl acetate. A mixed solution of the obtained filtrate and washing was analyzed with high-performance liquid chromatography. The yield of the target compound was 13.3% and 75.0% for a byproduct of methyl 3-methoxy-2-[2-(2-isopropoxy-6-trifluoromethylpyrimidin-4-on-3 -ylmethyl)phenyl]acrylate.

Workup

  1. customThe resulting suspension was reacted
  2. filtrationinsoluble matter was filtrated
  3. customThe precipitate separated by filtration
  4. washwas washed with 20 ml of etyl acetate
  5. washA mixed solution of the obtained filtrate and washing

Sources & evidence

ORD record
ord-93a30078671a4045959bcf87550e2afa
Source dataset
uspto-grants-2002_10
Patent number
US06462195B1

Reaction notes

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