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Process for preparing benzofuranone derivatives

A compound, the technology of trimethyl orthoformate, applied in the field of intermediates in the method of preparing phenoxypyrimidine compounds, can solve problems such as failure

Inactive Publication Date: 2002-12-18
ZENECA LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Unsuccessful attempts to formylate benzofuran-2(3H)one have been reported [see Journal of Organic Chemistry, 40(24) 3474-3480 (1975), A.D. Harmon and C.R. Hutchinson]

Method used

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  • Process for preparing benzofuranone derivatives

Examples

Experimental program
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Effect test

example 1

[0182] This example illustrates the preparation method of 3-(α-methoxy)methylenebenzofuran-2(3H)one.

[0183] Benzofuran-2(3H)one (10.2g), acetic anhydride (30ml) and trimethyl orthoformate (112.1g) were stirred at 100-105°C for 12 hours. During this period, a Dean-Stark device was used to collect low-boiling liquids.

[0184] The reaction mixture was allowed to cool and concentrated under reduced pressure (using a water bath temperature of 60°C) to obtain a brown solid. This solid was dissolved in dichloromethane (100ml), the solution was washed with water (2×50ml) and concentrated under reduced pressure (using a water bath temperature of 60°C) to obtain a crude product (13.5g). A part of the crude product was added to the crude product obtained from similar experiments, and the entire crude product was dissolved in methanol, and then treated with activated carbon. Thereafter, the methanol solution was refluxed for 30 minutes, cooled to below 10°C, filtered and the residue was wa...

example 2

[0188] This example illustrates another preparation method of 3-(α-methoxy)methylenebenzofuran-2(3H)one.

[0189] Ortho-hydroxyphenylacetic acid (15.2g), toluene (95ml) and glacial acetic acid (5ml) were mixed and heated to reflux for 4 hours, after which there was no undissolved raw material. During this period, water (2.2ml) was collected using a Dean-Stark device. Then, the reaction mixture was cooled and allowed to stand overnight.

[0190] Then acetic anhydride (40ml) was added to the reaction mixture and the low boiling point solvent (mostly toluene) (100ml) was distilled off. After cooling to below 50°C, trimethyl orthoformate (15.9 g) was added to the reaction mixture, and then the mixture was heated to 100-105°C for 20 hours. Gas chromatographic analysis showed that about 5% of the raw material remained.

[0191] The reaction mixture was worked up and purified as described in Example 1.

example 3

[0193] This example illustrates another preparation method of 3-(α-methoxy)methylenebenzofuran-2(3H)one.

[0194] Benzofuran-2(3H)one (10g), o-hydroxyphenylacetic acid (11.3g), acetic anhydride (60ml) and trimethyl orthoformate (23.7g) were heated to 100-105°C for 14 hours. During this period, a Dean-Stark device was used to collect some volatile products. Analysis of the reaction mixture indicated that about 5% of the starting material was still present.

[0195] The reaction mixture was concentrated under reduced pressure (water bath at 70°C) to obtain a crude product (28-24 g). This was combined with the crude product obtained from similar experiments and recrystallized from methanol to obtain the title compound.

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Abstract

Processes for the preparation of compounds (X), (XI) and (XII): <CHEM> <CHEM> <CHEM> where M is an alkali metal or alkaline earth metal and n is 1 or 2, and for obtaining compound (X) in a substantially pure form. These compounds are useful intermediates in the manufacture of fungicides.

Description

[0001] Related application [0002] This application is a divisional application of the invention patent application with the title of "Method for Preparing Phenoxypyrimidine Compound" and the application number of 91110782.7 filed on November 14, 1991. Technical field [0003] The patent application of the present invention relates to a method for preparing benzofuranone derivatives, which are intermediates in the method for preparing phenoxypyrimidine compounds. Background technique [0004] It is known that 3-(α-methoxy)methylenebenzofuran-2 can be prepared by methylating 3-formylbenzofuran-2(3H)-one with diazomethane or sulfuric acid in methanol. (3H)-ketone [see Australian Journal of Chemistry, 26(5) 1079-91 (1973), JAELix and BA Ferguson]. [0005] It has been reported that attempts to formylate benzofuran-2(3H) ketone were unsuccessful [see Journal of Organic Chemistry, 40(24)3474-3480 (1975), A.D.Harmon and C.R.Hutchinson]. Summary of the invention [0006] The present in...

Claims

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Application Information

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IPC IPC(8): C07D307/83C07DC07D239/34C07D239/52C07D307/28C07D307/86C07D311/12
CPCC07D239/34C07D307/83C07D311/12
Inventor J·D·琼斯G·A·迪布斯P·威尔金森J·M·菲尔登B·G·考克斯
Owner ZENECA LTD
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