3-[2-(ethoxycarbonyl)ethyl]-N-(3-pyridyl)indole → 3-(2-formylethyl)-N-(3-pyridyl)indole

HRID 485339Notes

Reaction equation

HRID 485339 reaction equation
C([O:3][C:4]([CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:9]=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl.C1(C)C=CC=CC=1>[CH:4]([CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:9]=1)=[O:3]

Participants

5

Reactant 2

HCID 202701823-[2-(ethoxycarbonyl)ethyl]-N-(3-pyridyl)indoleHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 134903543-(2-formylethyl)-N-(3-pyridyl)indole

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2.7 g of 3-[2-(ethoxycarbonyl)ethyl]-N-(3-pyridyl)indole in 50 ml of dry methylene chloride under nitrogen is cooled to -75° and 10.6 ml of 1.75M diisobutylaluminum hydride in toluene is added dropwise. The reaction is stirred for 8 minutes and quenched with 10 ml of water at -75°. Cooling is stopped and the layers are separated. The organic phase is washed with water, dried over potassium carbonate and evaporated to a solid which is recrystallized from ether-hexane to yield 3-(2-formylethyl)-N-(3-pyridyl)indole, m.p. 44°-45°.

Workup

  1. customquenched with 10 ml of water at -75°
  2. temperatureCooling
  3. customthe layers are separated
  4. washThe organic phase is washed with water
  5. dry with materialdried over potassium carbonate
  6. customevaporated to a solid which
  7. customis recrystallized from ether-hexane

Sources & evidence

ORD record
ord-7625907fc7ca40df970c49a316217051
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

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