Sodium Hydroxide → HCID 28806354, compound

HRID 1401092Notes

Reaction equation

HRID 1401092 reaction equation
C([O:3][C:4](=[O:17])/[CH:5]=[CH:6]/[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:16])[CH:14]=2)[NH:9][CH:8]=1)C.[OH-].[Na+]>C1COCC1.CO.O>[CH3:16][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2/[CH:6]=[CH:5]/[C:4]([OH:17])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86711434HCID 86711434, compound

Product 1

HCID 28806354HCID 28806354, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
50 °C

Procedure

(E)-ethyl-3-(5-methyl-1H-indol-3-yl)acrylate (1222.4 g, 5.33 mmol) prepared at Step 1 was dissolved in 32 ml of mixture solution (THF/methanol/H2O=2:1:1), after which NaOH acqueous solution (639.8 mg, 16.0 mmol) was added. After raising temperature to 50° C., stirring for 12 hr, neutralization with 10% hydrochoric acid to pH 4, and dilution with EtOAc, washing with water and brine, drying with anhydrous MgSO4, and concentration under reduced pressure followed. The concentrated residue was refined with silica gel chromatography (n-hexane:EtOAc=2:1) and dried to give target compound. (1070.5 mg, 99.8%).

Workup

  1. washneutralization with 10% hydrochoric acid to pH 4, and dilution with EtOAc, washing with water and brine
  2. dry with materialdrying with anhydrous MgSO4, and concentration under reduced pressure
  3. customdried
  4. customto give target compound

Sources & evidence

ORD record
ord-f7959032e54b4fc3885707db8d41a0de
Source dataset
uspto-grants-2014_12
Patent number
US08906952B2

Reaction notes

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