Water → HCID 21243289, compound

HRID 649632Notes

Reaction equation

HRID 649632 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:12](=O)[CH2:13][CH2:14][C:15]([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.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH3:1][O: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: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

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21243270HCID 21243270, compound

Product 1

HCID 21243289HCID 21243289, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 40.2 g of 2-[4-(5-methoxy-3-indolyl)-1,4-dioxobutyl]-1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridine [obtainable from 4-(5-methoxy-3-indolyl)-4-oxobutyric acid and 1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridine] in 3 l of hot absolute THF is added dropwise, with stirring, to a suspension of 23.4 g of LiAlH4 in 1100 ml of absolute THF, and the mixture is boiled for 1 hour, cooled, and decomposition is carried out with water and sodium hydroxide solution, and the usual working up is carried out. 2-[4-(5-methoxy-3-indolyl)butyl]-1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridine is obtained, Rf 0.5 (ethyl acetate).

Workup

  1. additionis added dropwise
  2. temperaturecooled

Sources & evidence

ORD record
ord-953bdeabbfde4023adecd895f47de5e4
Source dataset
uspto-grants-1988_04
Patent number
US04740602

Reaction notes

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