Indole → HCID 66608666, compound

HRID 221119Notes

Reaction equation

HRID 221119 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). (2) The above 4-ethylphenyl-(1H-indol-3-yl)methanol was treated in a manner similar to Reference Example 1-(2) to give the desired 3-(4-ethylphenylmethyl)-1H-indole as colorless crystals. APCI-Mass m/Z 236 (M+H).

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-0946c42ef9954d88a6abaa3df25ae37c
Source dataset
uspto-grants-2012_06
Patent number
US08202984B2

Reaction notes

Loading…