HCID 19870607, compound → HCID 19870622, compound

HRID 330183Notes

Reaction equation

HRID 330183 reaction equation
[OH:1][CH2:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:12][CH2:13][CH3:14])=[CH:8][NH:9]2)=[CH:5][CH:4]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:12][CH2:13][CH3:14])=[CH:8][NH:9]2)=[CH:5][CH:4]=1)=[O:1]

Participants

4

Reactant 1

HCID 19870607HCID 19870607, compound

Product 1

HCID 19870622HCID 19870622, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Manganese dioxide (5.05 g) was added in one portion to a sirred solution of 6-hydroxymethyl-3-propylindole (1.1 g) in methylene chloride (50 ml) under an atmosphere of nitrogen. The mixture was vigorously stirred for 60 min, filtered through a pad of diatomaceous earth, washing the pad several times with methylene chloride (5×30 ml). The filtrate was evaporated to give 6-formyl-3-propylindole (1.03 g, 95%) as a pale yellow oil; partial NMR (250 MHz, DMSO-d6): 0.93 (t, 3H, CH2CH3), 1.65(m, 2H, CH2CH3), 2.65(t, 2H, CH2CH2CH3), 9.98(s, 1H, CHO).

Workup

  1. filtrationfiltered through a pad of diatomaceous earth
  2. washwashing the pad several times with methylene chloride (5×30 ml)
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-66ccfe6401b54a6b8c941c2e6f939eb3
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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