(4R)-4-[(E)-2-(4-dimethylaminophenyl)ethenyl]-4-methyl-1,3-oxazolidin-2-one

Base Information

Chemical Name:(4R)-4-[(E)-2-(4-dimethylaminophenyl)ethenyl]-4-methyl-1,3-oxazolidin-2-one
CAS No.:1618092-47-9
Molecular Formula:C₁₄H₁₈N₂O₂
Molecular Weight:246.309
Hs Code.:

Synonyms:(4R)-4-[(E)-2-(4-dimethylaminophenyl)ethenyl]-4-methyl-1,3-oxazolidin-2-one

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Chemical Property of (4R)-4-[(E)-2-(4-dimethylaminophenyl)ethenyl]-4-methyl-1,3-oxazolidin-2-one

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Technology Process of (4R)-4-[(E)-2-(4-dimethylaminophenyl)ethenyl]-4-methyl-1,3-oxazolidin-2-one

There total 8 articles about (4R)-4-[(E)-2-(4-dimethylaminophenyl)ethenyl]-4-methyl-1,3-oxazolidin-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: 63.0%

: 1618092-42-4
{[(4S)-4-methyl-2-oxo-1,3-oxazolidin-4-yl]methyl}(triphenyl)phosphonium iodide

: 100-10-7
4-dimethylamino-benzaldehyde

: 1618092-47-9
(4R)-4-[(E)-2-(4-dimethylaminophenyl)ethenyl]-4-methyl-1,3-oxazolidin-2-one

Guidance literature:: {[(4S)-4-methyl-2-oxo-1,3-oxazolidin-4-yl]methyl}(triphenyl)phosphonium iodide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

4-dimethylamino-benzaldehyde; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 2h; diastereoselective reaction;
DOI:10.1016/j.tet.2014.05.086

Reference yield:

: 1618092-39-9
(4R)-4-(hydroxymethyl)-4-methyl-1,3-oxazolidin-2-one

: 1618092-47-9
(4R)-4-[(E)-2-(4-dimethylaminophenyl)ethenyl]-4-methyl-1,3-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: pyridine; p-toluenesulfonyl chloride / 3 h / 20 °C

1.2: 12 h / Reflux

2.1: N,N-dimethyl-formamide / 3 h / 110 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: 2 h / -78 - 20 °C

With pyridine; n-butyllithium; p-toluenesulfonyl chloride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 3.1: |Wittig Rearrangement;
DOI:10.1016/j.tet.2014.05.086

Reference yield:

: methyl (2R,4R)-4-[(benzyloxy)methyl]-2-tert-butyl-4-methyl-1,3-oxazolidine-3-carboxylate

: 1618092-47-9
(4R)-4-[(E)-2-(4-dimethylaminophenyl)ethenyl]-4-methyl-1,3-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: toluene-4-sulfonic acid / methanol / 1 h / Reflux

2.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C

3.1: potassium carbonate; palladium 10% on activated carbon; hydrogen / ethanol / 3 h

4.1: pyridine; p-toluenesulfonyl chloride / 3 h / 20 °C

4.2: 12 h / Reflux

5.1: N,N-dimethyl-formamide / 3 h / 110 °C

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.2: 2 h / -78 - 20 °C

With pyridine; n-butyllithium; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; potassium carbonate; toluene-4-sulfonic acid; p-toluenesulfonyl chloride; In tetrahydrofuran; methanol; ethanol; hexane; N,N-dimethyl-formamide; 6.1: |Wittig Rearrangement;
DOI:10.1016/j.tet.2014.05.086