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

HRID 850152Notes

Reaction equation

HRID 850152 reaction equation
C[O-].[Na+].[CH:4]([O:6][CH3:7])=[O:5].[Cl:8][C:9]1[N:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:23][C:24](OC)=[O:25])[CH:12]=[CH:11][CH:10]=1.O>C1(C)C=CC=CC=1>[Cl:8][C:9]1[N:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2/[C:23](=[CH:24]\[OH:25])/[C:4]([O:6][CH3:7])=[O:5])[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7865Methyl formateHCID 10942334Sodium MethoxideHCID 10989960Methyl 2-(6-chloropyrid-2-yloxymethyl)phenylacetate

Product 1

HCID 19366332(E)-methyl 2-[2-(6-chloropyrid-2-yloxymethyl)phenyl]-3-hydroxyacrylateYield 98.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Sodium methoxide (0.39 g, 6.9 mmol) and methyl formate (1 ml, 16 mmol) were added portionwise to a stirred solution of methyl 2-(6-chloropyrid-2-yloxymethyl)phenylacetate (1.0 g, 3.3 mmol) in dry toluene (15 ml) under a nitrogen atmosphere at room temperature. After 3 hours at room temperature the mixture was poured into water and extracted with ethyl acetate. The ethyl acetate extracts were washed with water, dried and the ethyl acetate removed to give (E)-methyl 2-[2-(6-chloropyrid-2-yloxymethyl)phenyl]-3-hydroxyacrylate (1.04 g, 95%) as a brown gum which was used in the final stage without further purification; 1H NMR(270 MHz)δ: 3.75(3H,s), 5.29(2H,s), 6.65(1H,d), 6,90(1H,d), 7.15-7.60(6H,m), 11.98(1H,d) ppm.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate extracts were washed with water
  3. customdried
  4. customthe ethyl acetate removed

Sources & evidence

ORD record
ord-09ee9767a3e54b42a9fead86d62e5dd3
Source dataset
uspto-grants-2000_01
Patent number
US06015905

Reaction notes

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