(E)-4-(5-Benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-enoic acid ethyl ester

Base Information

Chemical Name:(E)-4-(5-Benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-enoic acid ethyl ester
CAS No.:693784-44-0
Molecular Formula:C₂₆H₂₇BrO₆
Molecular Weight:515.401
Hs Code.:

Synonyms:(E)-4-(5-Benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-enoic acid ethyl ester

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Chemical Property of (E)-4-(5-Benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-enoic acid ethyl ester

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Technology Process of (E)-4-(5-Benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-enoic acid ethyl ester

There total 7 articles about (E)-4-(5-Benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-enoic acid ethyl ester 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:

: 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester

: (5-benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-acetaldehyde

: 693784-44-0
(E)-4-(5-Benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-enoic acid ethyl ester

Guidance literature:: With sodium hydride; In tetrahydrofuran; at -78 ℃;
DOI:10.1016/j.tetlet.2003.11.120

Reference yield:

: 93092-16-1
5-(benzyloxy)-2,3-dimethoxybenzaldehyde

: 693784-44-0
(E)-4-(5-Benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: NaH / tetrahydrofuran / 20 °C

1.2: 77 percent / TFA / H₂O / 20 °C

2.1: 92 percent / KOAc / Heating

3.1: K₂CO₃ / ethanol / 20 °C

4.1: LiAlH₄ / tetrahydrofuran / 20 °C

5.1: Pyr*HBr₃ / tetrahydrofuran / 0 °C

6.1: 93 percent / SO₃*Py; TEA; DMSO / CH₂Cl₂ / 20 °C

7.1: 94 percent / K₂CO₃ / dimethylformamide / 20 °C

8.1: 92 percent / NaH / dimethylsulfoxide; tetrahydrofuran / 0 °C

9.1: ZnBr₂ / benzene / Heating

10.1: NaH / tetrahydrofuran / -78 °C

With lithium aluminium tetrahydride; pyridine-SO₃ complex; TEA; potassium acetate; sodium hydride; potassium carbonate; dimethyl sulfoxide; pyridinium hydrobromide perbromide; zinc dibromide; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene; 1.1: Horner-Wadsworth-Emmons / 10.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.tetlet.2003.11.120

Reference yield:

: 693784-42-8
5-benzyloxy-3-bromo-4,7,8-trimethoxynaphthalene-2-carbaldehyde

: 693784-44-0
(E)-4-(5-Benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / NaH / dimethylsulfoxide; tetrahydrofuran / 0 °C

2: ZnBr₂ / benzene / Heating

3: NaH / tetrahydrofuran / -78 °C

With sodium hydride; zinc dibromide; In tetrahydrofuran; dimethyl sulfoxide; benzene; 3: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.tetlet.2003.11.120