Diethyl Ether → HCID 13520608, compound

HRID 1657013Notes

Reaction equation

HRID 1657013 reaction equation
[C:1]1([C:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([CH2:26][OH:27])[CH:24]=4)[NH:19][CH:18]=3)[CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCOCC>C1COCC1.O=[Mn]=O>[C:1]1([C:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([CH:26]=[O:27])[CH:24]=4)[NH:19][CH:18]=3)[CH2:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 13520598HCID 13520598, compound

Product 1

HCID 13520608HCID 13520608, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

36 g of 3-[4-(4-phenyl-1,2,3,6-tetrahydropyridyl)-butyl]-5-hydroxymethylindole are dissolved in 1.6 liters of THF, and 300 ml of ether are added. 55 g of MnO2 are added with stirring. The mixture is stirred for 16 hours at 20°, a further 100 g of MnO2 are added in portions, and stirring is continued for a further 100 hours at 20°. Filtration and working up in the customary manner gives 3-[4-(4-phenyl-1,2,3,6-tetrahydropyridyl)-butyl]-5-formylindole, m.p. 131°.

Workup

  1. stirringThe mixture is stirred for 16 hours at 20°
  2. stirringstirring
  3. filtrationFiltration

Sources & evidence

ORD record
ord-43756b5456b44d44b96936106eb231d1
Source dataset
uspto-grants-1993_10
Patent number
US05256673

Reaction notes

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