Water → HCID 86744724, compound

HRID 467052Notes

Reaction equation

HRID 467052 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][C:7]1[C:12](/[C:13](=[CH:18]\[O:19][CH3:20])/[C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:10]=[CH:9][N:8]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.O>ClCCl>[CH:2]([C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][C:7]1[C:12](/[C:13](=[CH:18]\[O:19][CH3:20])/[C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 2724130Cornforth reagentHCID 18650779HCID 18650779, compound

Product 1

HCID 86744724HCID 86744724, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (E)-methyl 2-[2-(3-hydroxymethylphenoxy)pyridin-3-yl]-3-methoxypropenoate (0.250 g) in dichloromethane (5 ml) at room temperature was added pyridinium dichromate (0.414 g). After stirring for 3 hours, GC analysis of an aliquot indicated the absence of starting material. Water was added and stirring continued for 10 minutes. The reaction mixture was filtered (filter washed through with water (5 ml) and dichloromethane (5 ml)) and then further diluted with dichloromethane (5 ml). The organic layer was separated and the aqueous phase further extracted with dichloromethane (×3). The combined organic layers were dried, filtered and evaporated to give a dark yellow oil. Chromatography on silica gel (eluent ether-petroleum ether, 7:3) afforded (E)-methyl 2-[2-(3-formylphenoxy)pyridin-3-yl]-3-methoxypropenoate (0.136g, 55%) as a white solid.

Workup

  1. stirringstirring
  2. waitcontinued for 10 minutes
  3. filtrationThe reaction mixture was filtered
  4. filtration(filter washed through with water (5 ml) and dichloromethane (5 ml))
  5. additionfurther diluted with dichloromethane (5 ml)
  6. customThe organic layer was separated
  7. extractionthe aqueous phase further extracted with dichloromethane (×3)
  8. customThe combined organic layers were dried
  9. filtrationfiltered
  10. customevaporated
  11. customto give a dark yellow oil

Sources & evidence

ORD record
ord-a2c98a77140c46d186eceb77c42d00c9
Source dataset
uspto-grants-1992_10
Patent number
US05158954

Reaction notes

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