Methanol → HCID 86682821, compound

HRID 1428172Notes

Reaction equation

HRID 1428172 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2/[CH:15]=[CH:16]/[C:17]([O:19]CC)=[O:18])=[CH:5][CH:4]=1.[OH-].[Na+].O1CCCC1.CO>O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 11448956HCID 11448956, compound

Product 1

HCID 86682821HCID 86682821, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl (2E)-3-[4-(4-methoxyphenyl)pyridin-3-yl]prop-2-enoate (2.75 g), 2M aqueous sodium hydroxide solution (7.3 mL), tetrahydrofuran (15 mL) and methanol (15 mL) was stirred at room temperature for 5 hr. To the reaction mixture was added water. The solvent was evaporated under reduced pressure, and the pH of the residue was adjusted to 5-6 with 10% aqueous citric acid solution. The precipitated solid was collected by filtration, washed with water and dried. The obtained solid was suspended in hot ethanol, and the suspension was stirred, and slowly cooled to room temperature. The suspension was filtered, and the obtained solid was washed with ethanol, and dried to give the title compound (2.12 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with water
  4. customdried
  5. stirringthe suspension was stirred
  6. temperatureslowly cooled to room temperature
  7. filtrationThe suspension was filtered
  8. washthe obtained solid was washed with ethanol
  9. customdried

Sources & evidence

ORD record
ord-9171b5950c904f25920f5d42efb66b5c
Source dataset
uspto-grants-2015_01
Patent number
US08937055B2

Reaction notes

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