(+/-)-(Z)-1-benzyl-3-[4-hydroxy-4-(2-methylphenyl)butan-2-ylidene]indolin-2-one

Base Information

Chemical Name:(+/-)-(Z)-1-benzyl-3-[4-hydroxy-4-(2-methylphenyl)butan-2-ylidene]indolin-2-one
CAS No.:1374606-09-3
Molecular Formula:C₂₆H₂₅NO₂
Molecular Weight:383.49
Hs Code.:

Synonyms:(+/-)-(Z)-1-benzyl-3-[4-hydroxy-4-(2-methylphenyl)butan-2-ylidene]indolin-2-one

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Chemical Property of (+/-)-(Z)-1-benzyl-3-[4-hydroxy-4-(2-methylphenyl)butan-2-ylidene]indolin-2-one

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Technology Process of (+/-)-(Z)-1-benzyl-3-[4-hydroxy-4-(2-methylphenyl)butan-2-ylidene]indolin-2-one

There total 5 articles about (+/-)-(Z)-1-benzyl-3-[4-hydroxy-4-(2-methylphenyl)butan-2-ylidene]indolin-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

: 1-benzyl-2-[(tert-butyldimethylsilyl)oxy]-3-(prop-1-en-2-yl)-1H-indole

: 529-20-4
2-methylphenyl aldehyde

: 1374606-09-3
(+/-)-(Z)-1-benzyl-3-[4-hydroxy-4-(2-methylphenyl)butan-2-ylidene]indolin-2-one

Guidance literature:: With tetrachlorosilane; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; at -20 ℃; for 12h; optical yield given as %de; Inert atmosphere;
DOI:10.1002/ejoc.201101446

Reference yield:

: 1217-89-6
1-benzylisatin

: 1374606-09-3
(+/-)-(Z)-1-benzyl-3-[4-hydroxy-4-(2-methylphenyl)butan-2-ylidene]indolin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / Inert atmosphere

1.2: 0.5 h / 20 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere; Cooling

3.1: tetrachlorosilane; N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 12 h / -20 °C / Inert atmosphere

With n-butyllithium; tetrachlorosilane; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 3.1: Mukaiyama aldol reaction;
DOI:10.1002/ejoc.201101446

Reference yield:

: 100-39-0
benzyl bromide

: 1374606-09-3
(+/-)-(Z)-1-benzyl-3-[4-hydroxy-4-(2-methylphenyl)butan-2-ylidene]indolin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

1.2: 0.5 h / 0 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / Inert atmosphere

2.2: 0.5 h / 20 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere; Cooling

4.1: tetrachlorosilane; N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 12 h / -20 °C / Inert atmosphere

With n-butyllithium; tetrachlorosilane; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; mineral oil; 4.1: Mukaiyama aldol reaction;
DOI:10.1002/ejoc.201101446