Hydrochloric Acid → HCID 19603206, compound

HRID 1160239Notes

Reaction equation

HRID 1160239 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6](/[CH:10]=[CH:11]/[C:12]([O:14]C)=[O:13])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Li+].[OH-].Cl>CO.O>[NH:1]1[C:9]2[C:4](=[CH:5][C:6](/[CH:10]=[CH:11]/[C:12]([OH:14])=[O:13])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 13707691HCID 13707691, compound

Product 1

HCID 19603206HCID 19603206, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of intermediate methyl (2E)-3-(1H-indol-5-yl)acrylate obtained from step 1 (255 mg, 1.27 mmol) in MeOH/H2O 5:1 (10 mL) was added solid LiOH (532 mg, 12.7 mmol) and the reaction mixture was stirred at room temperature overnight. The solution was acidified (pH ˜1) with HCl 1N and then extracted with ethyl acetate. The organic layer was washed with H2O (×3), then dried over sodium sulfate, filtered and evaporated under reduced pressure to give 0.24 g of intermediate E (2E)-3-(1H-indol-5-yl)acrylic acid (94% yield).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with H2O (×3)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-32284255ce434bfa9b3a24cd7a59f3d5
Source dataset
uspto-grants-2010_10
Patent number
US07816386B2

Reaction notes

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