Water → Picoxystrobin

HRID 850156Notes

Reaction equation

HRID 850156 reaction equation
S([O:6][CH3:7])(OC)(=O)=O.[F:8][C:9]([F:32])([F:31])[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:29]\O)/[C:25]([O:27][CH3:28])=[O:26])[CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:31][C:9]([F:8])([F:32])[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:29]\[O:6][CH3:7])/[C:25]([O:27][CH3:28])=[O:26])[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 19366334(E)-methyl 2-[2-(6-trifluoromethylpyrid-2-yloxymethyl)phenyl]-3-hydroxyacrylate

Product 1

HCID 11285653Picoxystrobin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dimethyl sulphate (0.65 ml, 6.9 mmol) was added dropwise to a mixture of (E)-methyl 2-[2-(6-trifluoromethylpyrid-2-yloxymethyl)phenyl]-3-hydroxyacrylate (2.12 g, 6 mmol) and anhydrous potassium carbonate (1.2 g, 8.7 mmol) in dry DMF (10 ml). After stirring at room temperature for 6 hours, the mixture was poured into water and extracted with diethyl ether. The ether extracts were washed with water, dried and concentrated to give a crude product which was purified by column chromatography (silica eluted with 20% ethyl acetate in hexane) to give (E)-methyl 2-[2-(6-trifluoromethylpyrid-2-yloxymethyl)phenyl]-3-methoxyacrylate (Compound No.177 in Table I of EP-A-0278595); (1.01 g, 46%) as a cream solid; mp 73-74° C.; 1H NMR (270 MHz)δ: 3.68(3H,s), 3.82(3H,s), 5.34(2H,s), 6.87(1H,d), 7.15-7.70(6H,m), 7.55(1H,s) ppm.

Workup

  1. extractionextracted with diethyl ether
  2. washThe ether extracts were washed with water
  3. customdried
  4. concentrationconcentrated
  5. customto give a crude product which
  6. customwas purified by column chromatography (silica eluted with 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-1d23e9924e724c0a82eb06fd0313be70
Source dataset
uspto-grants-2000_01
Patent number
US06015905

Reaction notes

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