tert-butyl-{3-methoxy-2-[3-methyl-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-5-phenethyl-phenoxy}-dimethyl-silane

Base Information

• Chemical Name: tert-butyl-{3-methoxy-2-[3-methyl-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-5-phenethyl-phenoxy}-dimethyl-silane
• CAS No.: 289472-19-1
• Molecular Formula: C₃₁H₄₆O₄Si
• Molecular Weight: 510.789

Synonyms:tert-butyl-{3-methoxy-2-[3-methyl-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-5-phenethyl-phenoxy}-dimethyl-silane

Chemical Property of tert-butyl-{3-methoxy-2-[3-methyl-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-5-phenethyl-phenoxy}-dimethyl-silane

Chemical Property:

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Technology Process of tert-butyl-{3-methoxy-2-[3-methyl-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-5-phenethyl-phenoxy}-dimethyl-silane

There total 7 articles about tert-butyl-{3-methoxy-2-[3-methyl-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-5-phenethyl-phenoxy}-dimethyl-silane 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: 68.0%

(Z)-<2-methyl-3-(2-tetrahydropyranyloxy)-1-propenyl>trimethylstannane (139896-11-0,126822-64-8) + (2-bromomethyl-3-methoxy-5-phenethyl-phenoxy)-tert-butyl-dimethyl-silane (289472-17-9) → tert-butyl-{3-methoxy-2-[3-methyl-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-5-phenethyl-phenoxy}-dimethyl-silane (289472-19-1)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; triphenyl-arsane; In 1,2-dimethoxyethane; at 85 ℃; for 24h;

DOI:10.1016/S0040-4039(00)00676-6

Reference yield:

1,3-dimethoxy-5-(2-phenylethyl)benzene (78916-50-4) → tert-butyl-{3-methoxy-2-[3-methyl-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-5-phenethyl-phenoxy}-dimethyl-silane (289472-19-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sec-BuLi; TMEDA / tetrahydrofuran

1.2: 91 percent / tetrahydrofuran

2.1: 87 percent / MgI₂*Et₂O / benzene / 3 h / Heating

3.1: NaH / tetrahydrofuran / 2 h / 20 °C

4.1: NaBH₄ / ethanol / 2.5 h / 0 °C

5.1: PBr₃; pyridine / diethyl ether / 0.5 h / 0 °C

6.1: 68 percent / Pd₂(dba)3; AsPh₃ / 1,2-dimethoxy-ethane / 24 h / 85 °C

With pyridine; sodium tetrahydroborate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; N,N,N,N,-tetramethylethylenediamine; triphenyl-arsane; sec.-butyllithium; phosphorus tribromide; sodium hydride; magnesium iodide; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; benzene; 1.1: Metallation / 1.2: Formylation / 2.1: demethylation / 3.1: silylation / 4.1: Reduction / 5.1: Bromination / 6.1: Stille coupling;

DOI:10.1016/S0040-4039(00)00676-6

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyl-{3-methoxy-2-[3-methyl-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-5-phenethyl-phenoxy}-dimethyl-silane (289472-19-1)

Guidance literature:

Multi-step reaction with 4 steps

1: NaH / tetrahydrofuran / 2 h / 20 °C

2: NaBH₄ / ethanol / 2.5 h / 0 °C

3: PBr₃; pyridine / diethyl ether / 0.5 h / 0 °C

4: 68 percent / Pd₂(dba)3; AsPh₃ / 1,2-dimethoxy-ethane / 24 h / 85 °C

With pyridine; sodium tetrahydroborate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; triphenyl-arsane; phosphorus tribromide; sodium hydride; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; 1: silylation / 2: Reduction / 3: Bromination / 4: Stille coupling;

DOI:10.1016/S0040-4039(00)00676-6

upstream raw materials:

(Z)-<2-methyl-3-(2-tetrahydropyranyloxy)-1-propenyl>trimethylstannane

(2-bromomethyl-3-methoxy-5-phenethyl-phenoxy)-tert-butyl-dimethyl-silane

1,3-dimethoxy-5-(2-phenylethyl)benzene

tert-butyldimethylsilyl chloride

Downstream raw materials:

2-[(Z)-3-Methyl-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-5-phenethyl-3-(tetrahydro-pyran-2-yloxy)-phenol

C₃₀H₄₀O₅

2-((Z)-4-Hydroxy-3-methyl-but-2-enyl)-3-methoxy-5-phenethyl-phenol

2-((Z)-4-Hydroxy-3-methyl-but-2-enyl)-5-phenethyl-benzene-1,3-diol

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