Diethyl Ether → 2-[4-(5-Formyl-3-indolyl)butyl]-1,2,3,4-tetrahydrobenzofuro-[2,3-c]pyridine

HRID 649635Notes

Reaction equation

HRID 649635 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][C:19]2[C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=3[O:24][C:18]=2[CH2:17]1.CCOCC>C1COCC1.O=[Mn]=O>[CH:2]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][C:19]2[C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=3[O:24][C:18]=2[CH2:17]1)=[O:1]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 212432642-[4-(5-Hydroxymethyl-3-indolyl)butyl]-1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridine

Product 1

HCID 212432602-[4-(5-Formyl-3-indolyl)butyl]-1,2,3,4-tetrahydrobenzofuro-[2,3-c]pyridine

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

37.4 g of 2-[4-(5-hydroxymethyl-3-indolyl)butyl]-1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridine are dissolved in 1.6 l of THF, and 300 ml of ether are added. While stirring, 55 g of MnO2 are added. The mixture is stirred at 20° for 16 hours, a further 100 g of MnO2 are added in portions, and the mixture is stirred at 20° for a further 100 hours. After filtration and the usual working up, 2-[4-(5-formyl-3-indolyl)butyl]-1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridine is obtained.

Workup

  1. stirringThe mixture is stirred at 20° for 16 hours
  2. stirringthe mixture is stirred at 20° for a further 100 hours
  3. filtrationAfter filtration

Sources & evidence

ORD record
ord-63ec048a3b844ca39193b14630232c87
Source dataset
uspto-grants-1988_04
Patent number
US04740602

Reaction notes

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