Ethanethiol → 2-(4-Hydroxyphenyl)benzo[b]thiophen-3-yl 4-[2-(1-Pyrrolidinyl)ethoxy]phenyl Ketone

HRID 650024Notes

Reaction equation

HRID 650024 reaction equation
COC.[N:4]1([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([C:20]3[C:21]4[CH:36]=[CH:35][CH:34]=[CH:33][C:22]=4[S:23][C:24]=3[C:25]3[CH:30]=[CH:29][C:28]([O:31]C)=[CH:27][CH:26]=3)=[O:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7][CH2:6][CH2:5]1.[Al+3].[Cl-].[Cl-].[Cl-].CCS>ClC(Cl)C>[N:4]1([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([C:20]3[C:21]4[CH:36]=[CH:35][CH:34]=[CH:33][C:22]=4[S:23][C:24]=3[C:25]3[CH:26]=[CH:27][C:28]([OH:31])=[CH:29][CH:30]=3)=[O:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 6343EthanethiolHCID 8254Dimethyl EtherHCID 6451240Aluminum(III) ChlorideHCID 98041622-(4-Methoxyphenyl)benzo[b]thiophen-3-yl 4-[2-(1-Pyrrolidinyl)ethoxy]phenyl Ketone

Product 1

HCID 183572252-(4-Hydroxyphenyl)benzo[b]thiophen-3-yl 4-[2-(1-Pyrrolidinyl)ethoxy]phenyl KetoneYield 33%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

By cleaving the methyl ether of 2-(4-methoxyphenyl)-benzo[b]thiophen-3-yl 4-[2-(1-pyrrolidinyl)ethoxy]phenyl ketone using AlCl3 (about 8 eq) and EtSH (about 10 eq) in dichloroethane at 0° C., the title compound was obtained in 33% yield as an oil following radial chromatography (SiO2; gradient of 2-10% MeOH in CH2Cl2).

Workup

  1. customat 0° C.

Sources & evidence

ORD record
ord-96ebf036b74047f8ac2332bdf1d15fb2
Source dataset
uspto-grants-2001_08
Patent number
US06271227B1

Reaction notes

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