Sodium Hydroxide → HCID 58213845, compound

HRID 1400667Notes

Reaction equation

HRID 1400667 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH:12]=[CH:11][CH:10]=[C:9]2/[CH:13]=[CH:14]/[C:15]([O:17]CC)=[O:16])=[CH:5][CH:4]=1.[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH:12]=[CH:11][CH:10]=[C:9]2/[CH:13]=[CH:14]/[C:15]([OH:17])=[O:16])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58213816HCID 58213816, compound

Product 1

HCID 58213845HCID 58213845, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of crude (E)-ethyl 3-(1-(4-methoxybenzyl)-1H-pyrrol-2-yl)acrylate in ethanol (50 mL) was added NaOH (1 g in 5 mL of H2O). After stirring 4 hr at room temperature, the solution was concentrated and then diluted with H2O (100 mL) and washed with TBME (2×75 mL). The aqueous base layer was the acidified with 1N HCl and extracted with ethyl acetate (100 mL). Then organic layer was dried (MgSO4), filtered and then concentrated to provide 0.92 g (59% for 3 steps) of (E)-3-(1-(4-methoxybenzyl)-1H-pyrrol-2-yl)acrylic acid as a light yellow solid.

Workup

  1. concentrationthe solution was concentrated
  2. additiondiluted with H2O (100 mL)
  3. washwashed with TBME (2×75 mL)
  4. extractionextracted with ethyl acetate (100 mL)
  5. dry with materialThen organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3a9584fbfa3e4b65bc01f50e925475dc
Source dataset
uspto-grants-2014_12
Patent number
US08906954B2

Reaction notes

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