HCID 54531533, compound → HCID 54239114, compound

HRID 845507Notes

Reaction equation

HRID 845507 reaction equation
C(O[N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH:18]=[CH:19][CH2:20][OH:21])=[CH:10]1)C1C=CC=CC=1>ClCCl.[O-2].[O-2].[Mn+4]>[CH2:11]([N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH:18]=[CH:19][CH:20]=[O:21])=[CH:10]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 54531533HCID 54531533, compound

Product 1

HCID 54239114HCID 54239114, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5 g (19 mmol) of 1-benzyloxy-3-(3-hydroxy-1 propen-1-yl) indole and 25 g of activated manganese dioxide in 500 ml of dichloromethane was stirred at room temperature for three hours and filtered through Celite®. The manganese compound was washed thoroughly with a mixture of dichloromethane and ethyl acetate until the Celite® layer was colorless. The combined filtrate and washing were concentrated on rotary evaporator and the residue was purified on a dry column (25% ethyl acetate in hexane) to give 2.3 g of 3-(1-benzylindol-3-yl)acrolein.

Workup

  1. filtrationfiltered through Celite®
  2. washThe manganese compound was washed thoroughly with a mixture of dichloromethane and ethyl acetate until the Celite® layer
  3. washThe combined filtrate and washing
  4. concentrationwere concentrated on rotary evaporator
  5. customthe residue was purified on a dry column (25% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b7eee36a12804b75967a8c5f909b5464
Source dataset
uspto-grants-1988_07
Patent number
US04758586

Reaction notes

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