4-Toluenesulfonyl chloride → HCID 13645493, compound

HRID 1074146Notes

Reaction equation

HRID 1074146 reaction equation
[CH3:1][C:2]1[N:3]([CH2:21][CH2:22][OH:23])[C:4]2[C:9]([C:10]=1[C:11](=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>N1C=CC=CC=1>[CH3:1][C:2]1[N:3]([CH2:21][CH2:22][O:23][S:30]([C:27]2[CH:28]=[CH:29][C:24]([CH3:34])=[CH:25][CH:26]=2)(=[O:32])=[O:31])[C:4]2[C:9]([C:10]=1[C:11](=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 10267331HCID 10267331, compound

Product 1

HCID 13645493HCID 13645493, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Following a procedure similar to that described above in Preparation 4A, 40 g. (0.015 mole) of 2-methyl-3-(4-methoxybenzoyl)indole in 320 ml. of THF was reacted with 61 ml. of a 2.6 M solution of butyl lithium in hexane and 45.8 ml. of ethylene oxide to give 33.6 g. (72%) of 2-methyl-3-(4-methoxybenzoyl)-1-(2-hydroxyethyl)-1H-indole. Reaction of 17 g. (0.06 mole) of the latter with 72 g. (0.06 mole) of p-toluenesulfonyl chloride in 250 ml. of pyridine afforded 2-methyl-3-(4-methoxybenzoyl)-1-(2-p-toluenesulfonyloxyethyl)-1H-indole as an oil.

Workup

  1. customReaction of 17 g

Sources & evidence

ORD record
ord-bcf82f45810b4894b890591b6b47e51e
Source dataset
uspto-grants-1990_11
Patent number
US04973587

Reaction notes

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