ethyl 4-[dimethyl(phenyl)silyl]-2-[(4-methoxyphenyl)imino]-4-(thiophen-2-yl)but-3-enoate

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Chemical Name:ethyl 4-[dimethyl(phenyl)silyl]-2-[(4-methoxyphenyl)imino]-4-(thiophen-2-yl)but-3-enoate
CAS No.:1595073-84-9
Molecular Formula:C₂₅H₂₇NO₃SSi
Molecular Weight:449.646
Hs Code.:

Synonyms:ethyl 4-[dimethyl(phenyl)silyl]-2-[(4-methoxyphenyl)imino]-4-(thiophen-2-yl)but-3-enoate

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Chemical Property of ethyl 4-[dimethyl(phenyl)silyl]-2-[(4-methoxyphenyl)imino]-4-(thiophen-2-yl)but-3-enoate

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Technology Process of ethyl 4-[dimethyl(phenyl)silyl]-2-[(4-methoxyphenyl)imino]-4-(thiophen-2-yl)but-3-enoate

There total 2 articles about ethyl 4-[dimethyl(phenyl)silyl]-2-[(4-methoxyphenyl)imino]-4-(thiophen-2-yl)but-3-enoate 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: 32.0%

: 1595074-63-7
ethyl 4-[dimethyl(phenyl)silyl]-2-oxo-4-(thiophen-2-yl)but-3-enoate

: 2101-87-3
p-methoxy-phenylazide

: 1595073-84-9
ethyl 4-[dimethyl(phenyl)silyl]-2-[(4-methoxyphenyl)imino]-4-(thiophen-2-yl)but-3-enoate

Guidance literature:: p-methoxy-phenylazide; With tributylphosphine; In tetrahydrofuran; at 20 ℃; for 2.5h; Inert atmosphere; Reflux;

ethyl 4-[dimethyl(phenyl)silyl]-2-oxo-4-(thiophen-2-yl)but-3-enoate; In tetrahydrofuran; for 1h; Optical yield = 82 %de; Reflux; Inert atmosphere;
DOI:10.1021/ol5007983

Reference yield:

: 3839-31-4
dimethyl(phenyl)silyl lithium

: 1595073-84-9
ethyl 4-[dimethyl(phenyl)silyl]-2-[(4-methoxyphenyl)imino]-4-(thiophen-2-yl)but-3-enoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: copper(l) cyanide / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere

1.2: 0.17 h / -85 - -20 °C / Inert atmosphere

2.1: tributylphosphine / tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere; Reflux

2.2: 1 h / Reflux; Inert atmosphere

With tributylphosphine; copper(l) cyanide; In tetrahydrofuran;
DOI:10.1021/ol5007983

Reference yield: 49.0%

: 1595073-84-9
ethyl 4-[dimethyl(phenyl)silyl]-2-[(4-methoxyphenyl)imino]-4-(thiophen-2-yl)but-3-enoate

: 925-90-6
ethylmagnesium bromide

: 100-52-7
benzaldehyde

: C₂₆H₂₇NO₃S

Guidance literature:: ethyl 4-[dimethyl(phenyl)silyl]-2-[(4-methoxyphenyl)imino]-4-(thiophen-2-yl)but-3-enoate; ethylmagnesium bromide; In tetrahydrofuran; at -78 - 40 ℃; for 0.5h; Inert atmosphere;

benzaldehyde; In tetrahydrofuran; for 1.5h; Inert atmosphere; Reflux;
DOI:10.1246/bcsj.20160402