Sodium Hydroxide → HCID 54202109, compound

HRID 566103Notes

Reaction equation

HRID 566103 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([CH:14]=[CH:15][C:16]([O:18]CC)=[O:17])[CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]([CH:14]=[CH:15][C:16]([OH:18])=[O:17])[CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Procedure

In methanol (5 ml) was suspended ethyl 6-(4-methylphenyl)-2-pyridineacrylate (465 mg, 1.74 mmol), and to the mixture was added at 0° C. 1N sodium hydroxide solution (5.22 ml). The mixture was stirred at room temperature for 20 hours. To the mixture was added at 0° C. 1N hydrochloric acid (5.22 ml), and methanol was evaporated under reduced pressure. The aqueous layer extracted with ethyl acetate (30 ml, 20 ml). The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure. To the residue was added diisopropylether(5 ml), and Insoluble materials were filtered, which were washed with diisopropylether and dried under reduced pressure to give 6-(4-methylphenyl)-2-pyridineacrylic acid (344 mg, 1.44 mmol, 83%).

Workup

  1. additionto the mixture was added at 0° C
  2. additionTo the mixture was added at 0° C
  3. custom1N hydrochloric acid (5.22 ml), and methanol was evaporated under reduced pressure
  4. extractionThe aqueous layer extracted with ethyl acetate (30 ml, 20 ml)
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionTo the residue was added diisopropylether(5 ml), and Insoluble materials
  8. filtrationwere filtered
  9. washwhich were washed with diisopropylether
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-c9039ac5938f446691457b16add50a66
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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