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Method for producing tetrahydropyran derivatives

A technology for tetrahydropyran derivatives and compounds, applied in the direction of organic chemistry, etc., can solve the problems of low convergence and divergence, and achieve the effects of high chemical and stereoselectivity, simple method and good yield

Active Publication Date: 2008-05-14
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this synthesis has low convergence and divergence, and using disubstituted homoallylic alcohols it is only possible to prepare precursors of 2,5-disubstituted tetrahydropyran derivatives with only a very restricted structural range

Method used

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  • Method for producing tetrahydropyran derivatives
  • Method for producing tetrahydropyran derivatives
  • Method for producing tetrahydropyran derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment A

[0181]

[0182] No. 3a,b - Table 1 A1 A2

[0183] 156 g (0.487 mol) of 4-bromo-2-(4-bromophenyl)tetrahydropyran (mixture of isomers 2,4-cis:2,4-trans) of number 3a,b in Table 1 formula = 84:16) and 87.2 ml (0.73 mol) of 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) in 330 ml of toluene with stirring at reflux for 3 hours, where During this time a suspension was formed. After cooling, the mixture was adjusted to pH 3 with 400 ml of water and dilute sulfuric acid and mixed vigorously. The organic phase was separated off with water and NaHCO 3 The solution was washed, filtered through silica gel and evaporated to give 105 g of a product mixture comprising A1 and A2 in a ratio of 65:35.

Embodiment B

[0185]

[0186] No. 2 - Table 3 B1

[0187] 49.7 g (0.15 mol) of isomer-pure 4-bromo-2-(4-bromophenyl)-5-methyltetrahydropyran numbered 2 in Table 3 were combined with 27.8 g (0.225 mol) of DBN was stirred in 200 ml of toluene at reflux for 4 h. The mixture was then cooled to 0°C and the salt precipitate was removed by filtration, and the filtrate was concentrated and filtered through silica gel using toluene / heptane (1:1). The filtrate was evaporated and the residue was crystallized from ethanol. The only isomer obtained was 4,5-dihydro-5-methyltetrahydropyran B1; yield (not optimized): 15.6 g (73%)

Embodiment C

[0189]

[0190] No. 3 - Table 3 C1

[0191] Similar to Example B, the tetrahydropyran derivative No. 3 in Table 3 (isomer mixture 2,4-cis:2,4-trans=85:15; 32.9 g, 0.107 mol) gave C1 , yield (without optimization): 89%.

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Abstract

The invention relates to a method for producing tetrahydropyran derivatives, to said tetrahydropyran derivatives and to the use of said tetrahydropyran derivative for producing other tetrahydropyran derivatives. The invention in particular relates to producing halogenated tetrahydropyran derivatives.

Description

technical field [0001] The present invention relates to a process for the preparation of tetrahydropyran derivatives, to these tetrahydropyran derivatives, and to the use of these tetrahydropyran derivatives for the preparation of other tetrahydropyran derivatives. The present invention particularly relates to the preparation of halogenated tetrahydropyran derivatives. Background technique [0002] Compounds having a tetrahydropyran ring as the central part of the molecule play an important role in organic chemistry, for example as constituents of natural or synthetic aroma substances, pharmaceuticals or mesogenic or liquid crystal compounds, or as used in the synthesis of these useful substances precursor. [0003] Of particular interest here are mesogenic or liquid crystalline tetrahydropyran derivatives with suitable (mesogenic) substituents, rings and / or ring systems in the 2- and / or 5-position, since they have some Advantageous for electro-optical and other physical p...

Claims

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Application Information

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IPC IPC(8): C07D309/08C07D309/28
CPCC07D309/08
Inventor E·珀奇W·宾德尔M·基施鲍姆R·舍费尔D·本辛格G·诺特纳格尔
Owner MERCK PATENT GMBH
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