(E)-(2-(hydroxymethyl)-5-oxo-4-(pyridin-2-ylmethylene)tetrahydrofuran-2-yl)methyl 4-(dimethylamino)benzoate

Base Information

Chemical Name:(E)-(2-(hydroxymethyl)-5-oxo-4-(pyridin-2-ylmethylene)tetrahydrofuran-2-yl)methyl 4-(dimethylamino)benzoate
CAS No.:1056461-88-1
Molecular Formula:C₂₁H₂₂N₂O₅
Molecular Weight:382.416
Hs Code.:

Synonyms:(E)-(2-(hydroxymethyl)-5-oxo-4-(pyridin-2-ylmethylene)tetrahydrofuran-2-yl)methyl 4-(dimethylamino)benzoate

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Chemical Property of (E)-(2-(hydroxymethyl)-5-oxo-4-(pyridin-2-ylmethylene)tetrahydrofuran-2-yl)methyl 4-(dimethylamino)benzoate

Chemical Property:

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Technology Process of (E)-(2-(hydroxymethyl)-5-oxo-4-(pyridin-2-ylmethylene)tetrahydrofuran-2-yl)methyl 4-(dimethylamino)benzoate

There total 5 articles about (E)-(2-(hydroxymethyl)-5-oxo-4-(pyridin-2-ylmethylene)tetrahydrofuran-2-yl)methyl 4-(dimethylamino)benzoate 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:

: 1056462-77-1
C₂₈H₂₈N₂O₅

: 1056461-88-1
(E)-(2-(hydroxymethyl)-5-oxo-4-(pyridin-2-ylmethylene)tetrahydrofuran-2-yl)methyl 4-(dimethylamino)benzoate

Guidance literature:: With boron trichloride; In dichloromethane; at -78 ℃;
DOI:10.1021/jm800380b

Reference yield:

: 1056463-07-0
C₂₆H₂₇NO₆

: 1056461-88-1
(E)-(2-(hydroxymethyl)-5-oxo-4-(pyridin-2-ylmethylene)tetrahydrofuran-2-yl)methyl 4-(dimethylamino)benzoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: methanesulfonyl chloride; triethylamine / dichloromethane / 2.5 h / 0 - 20 °C

1.2: 0 - 20 °C

2.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.5 h / 0 °C / Inert atmosphere

3.1: triethylamine; dmap / dichloromethane / 20 °C

4.1: boron trichloride / dichloromethane / -78 °C

With dmap; ammonium cerium (IV) nitrate; boron trichloride; methanesulfonyl chloride; triethylamine; In dichloromethane; water; acetonitrile;
DOI:10.1021/acs.jmedchem.8b00661

Reference yield:

: 213828-30-9
5-[(4-methoxyphenoxy)methyl]-5-[(phenylmethoxy)methyl]-3,4,5-trihydrofuran-2-one

: 1056461-88-1
(E)-(2-(hydroxymethyl)-5-oxo-4-(pyridin-2-ylmethylene)tetrahydrofuran-2-yl)methyl 4-(dimethylamino)benzoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C / Inert atmosphere

1.2: -78 - 20 °C

2.1: methanesulfonyl chloride; triethylamine / dichloromethane / 2.5 h / 0 - 20 °C

2.2: 0 - 20 °C

3.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.5 h / 0 °C / Inert atmosphere

4.1: triethylamine; dmap / dichloromethane / 20 °C

5.1: boron trichloride / dichloromethane / -78 °C

With dmap; ammonium cerium (IV) nitrate; boron trichloride; methanesulfonyl chloride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; acetonitrile; 1.1: |Aldol Addition / 1.2: |Aldol Addition;
DOI:10.1021/acs.jmedchem.8b00661