(E-trans)-4-(tert-butyldimethylsiloxy)-6-<2-(2,4-dichlorophenyl)ethenyl>-3,4,5,6-tetrahydro-2H-pyran-2-one

Base Information

Chemical Name:(E-trans)-4-(tert-butyldimethylsiloxy)-6-<2-(2,4-dichlorophenyl)ethenyl>-3,4,5,6-tetrahydro-2H-pyran-2-one
CAS No.:83268-72-8
Molecular Formula:C₁₉H₂₆Cl₂O₃Si
Molecular Weight:401.405
Hs Code.:

Synonyms:(E-trans)-4-(tert-butyldimethylsiloxy)-6-<2-(2,4-dichlorophenyl)ethenyl>-3,4,5,6-tetrahydro-2H-pyran-2-one

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Chemical Property of (E-trans)-4-(tert-butyldimethylsiloxy)-6-<2-(2,4-dichlorophenyl)ethenyl>-3,4,5,6-tetrahydro-2H-pyran-2-one

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Technology Process of (E-trans)-4-(tert-butyldimethylsiloxy)-6-<2-(2,4-dichlorophenyl)ethenyl>-3,4,5,6-tetrahydro-2H-pyran-2-one

There total 1 articles about (E-trans)-4-(tert-butyldimethylsiloxy)-6-<2-(2,4-dichlorophenyl)ethenyl>-3,4,5,6-tetrahydro-2H-pyran-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: 90.0%

: 86097-37-2
trans-(E)-6-[2-(2,4-dichlorophenyl)ethenyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one

: 18162-48-6
tert-butyldimethylsilyl chloride

: 83268-72-8
(E-trans)-4-(tert-butyldimethylsiloxy)-6-<2-(2,4-dichlorophenyl)ethenyl>-3,4,5,6-tetrahydro-2H-pyran-2-one

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 16h; Ambient temperature;
DOI:10.1021/jo00145a029

Reference yield: 94.0%

: 83268-72-8
(E-trans)-4-(tert-butyldimethylsiloxy)-6-<2-(2,4-dichlorophenyl)ethenyl>-3,4,5,6-tetrahydro-2H-pyran-2-one

: 83268-73-9,83348-93-0
(E)-4β-(tert-butyldimethylsiloxy)-6α-<2-(2,4-dichlorophenyl)ethenyl>-3,4,5,6-tetrahydro-2H-pyran-2-ol

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;
DOI:10.1021/jo00145a029

Reference yield:

: 83268-72-8
(E-trans)-4-(tert-butyldimethylsiloxy)-6-<2-(2,4-dichlorophenyl)ethenyl>-3,4,5,6-tetrahydro-2H-pyran-2-one

: 83268-76-2
(E-trans)-5-(tert-butyldimethylsiloxy)-7-<2-(2,4-dichlorophenyl)ethenyl>hexahydrooxepin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / diisobutylaluminum hydride / hexane; tetrahydrofuran / 0.5 h / -78 °C

2: 1.) n-butyllithium / 1.) hexane, THF, from -70 deg C to room temp., 70 min, 2.) from -70 deg C to room temp.

3: pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / Ambient temperature

4: 88 percent / cadmium carbonate, silver nitrate / acetonitrile; tetrahydrofuran; H₂O / 1 h / Ambient temperature

With n-butyllithium; cadmium(II) carbonate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; silver nitrate; In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile;
DOI:10.1021/jo00145a029