Water → (E)-methyl 2-[2-(6-trifluoromethylpyrid-2-yloxymethyl)phenyl]-3-hydroxyacrylate

HRID 850155Notes

Reaction equation

HRID 850155 reaction equation
C[O-].[Na+].[CH:4]([O:6][CH3:7])=[O:5].[F:8][C:9]([F:30])([F:29])[C:10]1[N:15]=[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH2:24][C:25](OC)=[O:26])[CH:13]=[CH:12][CH:11]=1.O>C1(C)C=CC=CC=1>[F:29][C:9]([F:8])([F:30])[C:10]1[N:15]=[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2/[C:24](=[CH:25]\[OH:26])/[C:4]([O:6][CH3:7])=[O:5])[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7865Methyl formateHCID 10860344Metabolite 10 of PicoxystrobinHCID 10942334Sodium Methoxide

Product 1

HCID 19366334(E)-methyl 2-[2-(6-trifluoromethylpyrid-2-yloxymethyl)phenyl]-3-hydroxyacrylateYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Sodium methoxide (0.725 g, 13 mmol) and methyl formate (0.8 ml, 13 mmol) were added portionwise to a stirred solution of methyl 2-(6-trifluoromethylpyrid-2-yloxymethyl)phenylacetate (2.0 g, 6.0 mmol) in dry toluene (15 ml) under a nitrogen atmosphere at room temperature. After 6 hours at room temperature, the mixture was poured into water and extracted with diethyl ether. The ether extracts were washed with water, dried and the ether removed to give (E)-methyl 2-[2-(6-trifluoromethylpyrid-2-yloxymethyl)phenyl]-3-hydroxyacrylate (2.01 g, 95%) as a yellow gum which was used in the next stage without further purification; 1H NMR (270 MHz)δ: 3.75(3H,s), 5.34(2H,s), 6.90(1H,d), 7.15-7.75(7H,m), 11.95(1H,d) ppm.

Workup

  1. extractionextracted with diethyl ether
  2. washThe ether extracts were washed with water
  3. customdried
  4. customthe ether removed

Sources & evidence

ORD record
ord-c7c04b83a3e14e2491d350f24235ee4b
Source dataset
uspto-grants-2000_01
Patent number
US06015905

Reaction notes

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