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Formation of chromanes and chromenes by using silver(i) or gold(i) salts or complexes

A technology of complexes and compounds, applied in the direction of organic chemistry, etc.

Active Publication Date: 2016-04-06
DSM IP ASSETS BV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Furthermore, it mentions that the use of Ag(I) leads to an unexpected dimerization of the desired chromene
[0013] However, none of said documents addresses the formation of chiral chromene entities of the desired structure by using hydroaromatization at low temperatures and with high yields

Method used

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  • Formation of chromanes and chromenes by using silver(i) or gold(i) salts or complexes
  • Formation of chromanes and chromenes by using silver(i) or gold(i) salts or complexes
  • Formation of chromanes and chromenes by using silver(i) or gold(i) salts or complexes

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Experimental program
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Embodiment

[0198] The invention is further illustrated by the following experiments.

[0199] Analytical method

[0200] Gas Chromatography (GC):

[0201] GC analysis has been performed on an Agilent HP-6850 series system using FID-detector and using helium as a carrier gas. Separation was achieved on a HP-1 methylsiloxane (30 m x 0.32 mm, 0.25 μm) column using the following temperature programming: 50 °C (0 min) -> 10 °C / min -> 300 °C (5 min) . Samples were dissolved in ethyl acetate (5 mg sample in 1 mL ethyl acetate) and 1 μL of the solution was injected in a 50:1 split ratio.

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Abstract

The present invention relates to the method of preparing chiral chromanes and chromenes in high yields by intramolecular hydroarylation of chiral aryl alkynes catalysed by either a silver(I) or gold(I) salt or complex in combination of a specific acid or by a silver(I) or gold(I) metal salt or complex having specific anion. By the hydroarylation a chromene is formed which has a chiral centre in the 2 position. The corresponding chromane is obtained by hydrogenation of the chromenes.

Description

technical field [0001] The present invention relates to the field of synthesis of chromanes and chromenes, in particular (3,4)-dehydrotocopherol, (3,4)-dehydrotocotrienol, tocopherol and tocotriene phenol. Background technique [0002] An important class of chromane compounds is vitamin E and its esters. Vitamin E is often commercialized in its ester form because it exhibits enhanced stability, especially against humidity, air, and oxidizing agents. [0003] On the one hand the typical technical synthesis of vitamin E produces a mixture of isomers. On the other hand, higher biological activity (biopotency) has been shown to generally be due to the fact that tocopherols and tocotrienols are located in the ether in the molecular ring compared to the enantiomers with the S configuration Chiral centers in the vicinity of the atoms (indicated by * in formulas used later in this document) have the R configuration (ie, the 2R configuration). Especially active are tocopherol iso...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/70C07D311/72
CPCC07D311/70C07D311/72
Inventor 尤拉·莱提诺伊斯托马斯·内切尔雷奈·托拜厄斯·史德姆勒
Owner DSM IP ASSETS BV
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