(R)-3-(3-(benzyloxy)-2-ethynylphenyl)-3-((2-(trimethylsilyl)ethoxy)methoxy)but-an-2-one

Base Information

Chemical Name:(R)-3-(3-(benzyloxy)-2-ethynylphenyl)-3-((2-(trimethylsilyl)ethoxy)methoxy)but-an-2-one
CAS No.:1410804-96-4
Molecular Formula:C₂₅H₃₂O₄Si
Molecular Weight:424.612
Hs Code.:

Synonyms:(R)-3-(3-(benzyloxy)-2-ethynylphenyl)-3-((2-(trimethylsilyl)ethoxy)methoxy)but-an-2-one

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Chemical Property of (R)-3-(3-(benzyloxy)-2-ethynylphenyl)-3-((2-(trimethylsilyl)ethoxy)methoxy)but-an-2-one

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Technology Process of (R)-3-(3-(benzyloxy)-2-ethynylphenyl)-3-((2-(trimethylsilyl)ethoxy)methoxy)but-an-2-one

There total 6 articles about (R)-3-(3-(benzyloxy)-2-ethynylphenyl)-3-((2-(trimethylsilyl)ethoxy)methoxy)but-an-2-one 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: 98.0%

: 1410804-95-3
(R)-3-(3-(benzyloxy)-2-ethynylphenyl)-3-hydroxybutan-2-one

: 76513-69-4
(2-trimethylethylsilylethoxy)methyl chloride

: 1410804-96-4
(R)-3-(3-(benzyloxy)-2-ethynylphenyl)-3-((2-(trimethylsilyl)ethoxy)methoxy)but-an-2-one

Guidance literature:: With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 40 ℃; for 20h; Inert atmosphere;
DOI:10.1021/ol302691j

Reference yield:

: 22532-61-2
2-bromo-6-hydroxybenzaldehyde

: 1410804-96-4
(R)-3-(3-(benzyloxy)-2-ethynylphenyl)-3-((2-(trimethylsilyl)ethoxy)methoxy)but-an-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 14 h / 20 °C / Inert atmosphere

2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 3 h / -78 - 20 °C / Inert atmosphere

3.1: n-butyllithium / hexane; tetrahydrofuran / 0.42 h / -70 - 20 °C / Inert atmosphere

3.2: 1.25 h / -78 - 20 °C / Inert atmosphere

3.3: 14 h / 0 °C / Inert atmosphere

4.1: triethylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide / 1.25 h / 0 °C / Inert atmosphere

5.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 20 h / 40 °C / Inert atmosphere

With n-butyllithium; sulfur trioxide pyridine complex; tetra-(n-butyl)ammonium iodide; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/ol302691j

Reference yield:

: 1410804-93-1
((2-(benzyloxy)-6-bromophenyl)ethynyl)trimethylsilane

: 1410804-96-4
(R)-3-(3-(benzyloxy)-2-ethynylphenyl)-3-((2-(trimethylsilyl)ethoxy)methoxy)but-an-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 0.42 h / -70 - 20 °C / Inert atmosphere

1.2: 1.25 h / -78 - 20 °C / Inert atmosphere

1.3: 14 h / 0 °C / Inert atmosphere

2.1: triethylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide / 1.25 h / 0 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 20 h / 40 °C / Inert atmosphere

With n-butyllithium; sulfur trioxide pyridine complex; tetra-(n-butyl)ammonium iodide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/ol302691j