(E)-4-(5-Benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-en-1-ol

Base Information

Chemical Name:(E)-4-(5-Benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-en-1-ol
CAS No.:693784-38-2
Molecular Formula:C₂₄H₂₅BrO₅
Molecular Weight:473.364
Hs Code.:

Synonyms:(E)-4-(5-Benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-en-1-ol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (E)-4-(5-Benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-en-1-ol

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Technology Process of (E)-4-(5-Benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-en-1-ol

There total 7 articles about (E)-4-(5-Benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-en-1-ol 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: 93.0%

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

: 693784-38-2
(E)-4-(5-Benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-en-1-ol

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

Reference yield:

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

: 693784-38-2
(E)-4-(5-Benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 11 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

11.1: 93 percent / DIBAL / tetrahydrofuran / -78 °C

With lithium aluminium tetrahydride; pyridine-SO₃ complex; TEA; potassium acetate; sodium hydride; diisobutylaluminium 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

: 693784-38-2
(E)-4-(5-Benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 4 steps

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

2: ZnBr₂ / benzene / Heating

3: NaH / tetrahydrofuran / -78 °C

4: 93 percent / DIBAL / tetrahydrofuran / -78 °C

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