ethyl (2E)-4-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-2-naphthyl)but-2-enoate

Base Information

Chemical Name:ethyl (2E)-4-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-2-naphthyl)but-2-enoate
CAS No.:809231-33-2
Molecular Formula:C₂₆H₂₇BrO₆
Molecular Weight:515.401
Hs Code.:

Synonyms:ethyl (2E)-4-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-2-naphthyl)but-2-enoate

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Chemical Property of ethyl (2E)-4-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-2-naphthyl)but-2-enoate

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Technology Process of ethyl (2E)-4-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-2-naphthyl)but-2-enoate

There total 8 articles about ethyl (2E)-4-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-2-naphthyl)but-2-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:

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

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

: 809231-33-2
ethyl (2E)-4-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-2-naphthyl)but-2-enoate

Guidance literature:: diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1.5h;

(5-benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-acetaldehyde; In tetrahydrofuran; at -78 - 0 ℃; for 0.416667h;
DOI:10.1246/bcsj.77.1925

Reference yield:

: 693784-41-7
8-benzyloxy-3-hydroxymethyl-5,6-dimethoxy-1-naphthol

: 809231-33-2
ethyl (2E)-4-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-2-naphthyl)but-2-enoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: pyridine*HBr₃ / tetrahydrofuran / 1 h / 0 °C

2.1: SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 0.33 h / 20 °C

3.1: 2.32 g / K₂CO₃ / dimethylformamide / 1 h / 20 °C

4.1: NaH; DMSO / tetrahydrofuran / 0.67 h / 0 - 5 °C

4.2: tetrahydrofuran; dimethylsulfoxide / 0.92 h / 0 °C

5.1: ZnBr₂ / benzene / 0.33 h / Heating

6.1: NaH / tetrahydrofuran / 1.5 h / 0 °C

6.2: 1.77 g / tetrahydrofuran / 0.42 h / -78 - 0 °C

With pyridinium perbromide hydrobromide; pyridine-SO₃ complex; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; zinc dibromide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene; 6.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1246/bcsj.77.1925

Reference yield:

: 693784-36-0
8-benzyloxy-2-bromo-3-hydroxymethyl-5,6-dimethoxy-naphthalen-1-ol

: 809231-33-2
ethyl (2E)-4-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-2-naphthyl)but-2-enoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 0.33 h / 20 °C

2.1: 2.32 g / K₂CO₃ / dimethylformamide / 1 h / 20 °C

3.1: NaH; DMSO / tetrahydrofuran / 0.67 h / 0 - 5 °C

3.2: tetrahydrofuran; dimethylsulfoxide / 0.92 h / 0 °C

4.1: ZnBr₂ / benzene / 0.33 h / Heating

5.1: NaH / tetrahydrofuran / 1.5 h / 0 °C

5.2: 1.77 g / tetrahydrofuran / 0.42 h / -78 - 0 °C

With pyridine-SO₃ complex; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; zinc dibromide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene; 5.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1246/bcsj.77.1925