Indole → HCID 66608666, compound

HRID 1625860Notes

Reaction equation

HRID 1625860 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[Na+].[CH2:12]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1)[CH3:13].O>CO>[CH2:12]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[OH:19])=[CH:16][CH:15]=1)[CH3:13]

Participants

6

Reactant 4

HCID 798IndoleHCID 962WaterHCID 14798Sodium HydroxideHCID 208614-Ethylbenzaldehyde

Product 1

HCID 66608666HCID 66608666, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of indole (6.00 g) in methanol (60 ml) were added sodium hydroxide (2.25 g) and 4-ethylbenzaldehyde (7.56 g), and the mixture was stirred at room temperature for 3 days under argon atmosphere. Added thereto was water, and methanol was evaporated under reduced pressure. The residue was extracted with diethyl ether, and the extract was washed with water, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=98:2-70:30) to give 4-ethylphenyl-(1H-indol-3-yl)methanol (2.10 g) as a colorless solid. APCI-Mass m/Z 234 (M+H−H2O).

Workup

  1. additionAdded
  2. customwas evaporated under reduced pressure
  3. extractionThe residue was extracted with diethyl ether
  4. washthe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=98:2-70:30)

Sources & evidence

ORD record
ord-dda5900f2d84499ebf1eccab08a5a6b3
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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