Indole → 159884-46-5

HRID 618564Notes

Reaction equation

HRID 618564 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH2:12]([O:14][CH:15]([O:18][CH2:19][CH3:20])[CH2:16]Br)[CH3:13].O>CS(C)=O>[CH2:12]([O:14][CH:15]([O:18][CH2:19][CH3:20])[CH2:16][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)[CH3:13]

Participants

6

Reactant 4

HCID 798IndoleHCID 962WaterHCID 24758Sodium hydrideHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 22013069159884-46-5

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 12 g of indole in 100 ml of dimethyl sulfoxide was added 6.5 g of sodium hydride at room temperature. The mixture was stirred at the same temperature for 1 hour, and 20 ml of bromoacetaldehyde diethyl acetal was added thereto, followed by further stirring at 50° C. for 1 hour. After cooling, the reaction mixture was poured into water, and the product was extracted with ethyl ether. The organic layer was dried over anhydrous magnesium sulfate and concentrated to give 23 g of the title compound.

Workup

  1. stirringby further stirring at 50° C. for 1 hour
  2. temperatureAfter cooling
  3. extractionthe product was extracted with ethyl ether
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c73b62df06bc4bacbbb239556889a14b
Source dataset
uspto-grants-1999_09
Patent number
US05952511

Reaction notes

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