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Synthetic method of 3-fluorophenyl-4-methylol cyclopentanone

A technology of hydroxymethylcyclopentanone and m-fluorophenyl, which is applied in the field of synthesis of organic compounds, and achieves the effects of cheap reagents, mild reaction conditions and easy operation

Inactive Publication Date: 2012-11-07
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The specific reaction process is shown in formula 3

Method used

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  • Synthetic method of 3-fluorophenyl-4-methylol cyclopentanone
  • Synthetic method of 3-fluorophenyl-4-methylol cyclopentanone
  • Synthetic method of 3-fluorophenyl-4-methylol cyclopentanone

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Experimental program
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Effect test

Embodiment 1

[0027] Will (EtO) 2 P(O)CH 2 COOEt was dissolved in tetrahydrofuran, then sodium hydride was added to it, and after stirring for 30 minutes, m-fluorobenzaldehyde was added thereto, and then heated to reflux until one raw material disappeared, quenched with water, extracted with ethyl acetate, and the organic phase was dried and evaporated to dryness Afterwards, the residue was purified by silica gel column chromatography to obtain the target compound 10. (EtO) 2 P(O)CH 2 The molar ratio of COOE to sodium hydride and m-fluorobenzaldehyde was 1.2:1.2:1.0 and the reaction yield was 81% when the reaction was carried out for 20 hours.

[0028] Compound 10 was dissolved in ether, and under the protection of argon, the reaction solution was cooled to below minus 40 degrees Celsius, and then lithium aluminum hydride was slowly added thereto (the molar weight of lithium aluminum hydride was less than 1.5 times the molar weight of compound 10), Continue stirring at low temperature u...

Embodiment 2

[0035] BrPPh 3 CH 2 COOEt is dissolved in CH 2 Cl 2 , and then drop aqueous sodium hydroxide solution into it, stir and react for five minutes, separate liquids, dry the organic phase and evaporate to dryness, dissolve in toluene, and add m-fluorobenzaldehyde to it, then heat and reflux until one raw material disappears, evaporate After drying, the residue was purified by silica gel column chromatography to obtain the target compound 10. BrPPh 3 CH 2 When the molar ratio of COOEt to sodium hydroxide and m-fluorobenzaldehyde was 1.2:1.2:1.0 and the reaction was carried out for 20 hours, the reaction yield was 85%.

[0036] Compound 10 was dissolved in tetrahydrofuran, and under the protection of argon, the reaction solution was cooled to below minus 10 degrees Celsius, and then lithium aluminum hydride was slowly added thereto (the molar weight of lithium aluminum hydride was less than 1.5 times the molar weight of compound 10), Continue stirring at low temperature until ...

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Abstract

The invention discloses a synthetic method of 3-fluorophenyl-4-methylol cyclopentanone. M-fluorobenzaldehyde is used as initial raw materials. The synthetic method comprises the following steps of: firstly, synthesizing an m-difluorobenzene acrylic ester compound through Wittig reaction; then reducing the compound into an m-difluorobenzene allyl alcohol compound; further converting the m-difluorobenzene allyl alcohol compound into an acetoacetic acid m-difluorobenzene acrylic ester compound; converting the compound into a 4-(3-fluorophenyl)-5-hexenyl-2-ketone compound through rearrangement reaction under the condition of heating; converting the compound into a 6-(3-fluorophenyl)-3-oxo-7-octenoic acid ester compound, then carrying out ring opening and decarboxylation on a reactant under the action of alkaline through series cyclization reaction to obtain the target compound, i.e. the 3-fluorophenyl-4-methylol cyclopentanone.

Description

technical field [0001] The present invention relates to a method for synthesizing an organic compound, specifically a method for synthesizing 3-m-fluorophenyl-4-hydroxymethylcyclopentanone. The structure of the compound is shown in Formula 1. [0002] [0003] Formula 1 Background technique [0004] Many substituted cyclopentanones have been found to have very important biopharmacological activities. There are also quite a few compounds containing cyclopentanone fragments that are used in the development of new drugs. They are also important intermediates for many pharmaceutical products. Literature M.Palucki, J.M.Um, N.Yasuda, D.A.Conlon, F.-R.Tsay, F.W.Hartner, Y.Hsiao, B.Marcune, S.Karady, D.L.Hughes, P.G.Dormer, P.J.Reider, J.Org. Chem.2002, 67, 5508-5516 discloses that the compound shown in formula 1 is the key intermediate of a new drug being developed by Merck, and a synthetic formula 1 provided by Merck in 2002 is also disclosed in this document. The route of ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/747C07C45/65
Inventor 张虹锐薛吉军李瀛唐瑜郑保富
Owner LANZHOU UNIVERSITY