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

HRID 649636Notes

Reaction equation

HRID 649636 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][C:20]2[C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=3[O:25][C:19]=2[CH2:18]1)(O)=[O:2].[H-].C([Al+]CC(C)C)C(C)C.O>C1(C)C=CC=CC=1>[CH:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][C:20]2[C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=3[O:25][C:19]=2[CH2:18]1)=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 21243293HCID 21243293, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

3.88 g of 2-[4-(5-carboxy-3-indolyl)butyl]-1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridine are suspended in 25 ml of toluene and, under N2 and while stirring, 3 time the molar amount of a 20% solution of diisobutylaluminium hydride in toluene is added dropwise, and the mixture is boiled for 2 hours, cooled, decomposition is carried out with water, the usual working up is carried out, and 2-[4-(5-formyl-3-indolyl)butyl]-1,2,3,4-tetrahydrobenzofuro-[2,3-c]pyridine is obtained.

Workup

  1. temperaturecooled

Sources & evidence

ORD record
ord-50f581679d4d4696b9490a1ebac8f9ac
Source dataset
uspto-grants-1988_04
Patent number
US04740602

Reaction notes

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