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US08008514B2 Process for preparing 2-methoxycarbonylmethyl-6,6-dimethyl-2-tetrahydropyran carboxylic acid 失效
制备2-甲氧基羰基甲基-6,6-二甲基-2-四氢吡喃羧酸的方法

Process for preparing 2-methoxycarbonylmethyl-6,6-dimethyl-2-tetrahydropyran carboxylic acid
Abstract:
Process for preparing 2-methoxycarbonylmethyl-6,6-dimethyl-2-tetrahydropyran carboxylic acid (I) comprising: a) Reaction of 5-bromo-2-methyl-2-pentene (III) with magnesium and then diethyloxalate to obtain ethyl-2-oxo-6-methyl-5-heptenoate (IV); b) Reaction of ethyl-2-oxo-6-methyl-5-heptenoate (IV) with an alkali amide and methyl acetate to obtain ethyl-2-methoxycarbonylmethyl-2-hydroxy-6-methyl-5-heptenoate (V); c) Reaction of ethyl-2-methoxycarbonylmethyl-2-hydroxy-6-methyl-5-heptenoate (V) with an alkali metal hydroxide to obtain the corresponding 2-carboxymethyl-2-hydroxy-6-methyl-5-heptenoic acid (VI); d) Cyclisation of 2-carboxymethyl-2-hydroxy-6-methyl-5-heptenoic acid (VI) with formic acid to give 2-carboxymethyl-6,6-dimethyl-2-tetrahydropyrancarboxylic acid (VII); e) Monoesterification of 2-carboxymethyl-6,6-dimethyl-2-tetrahydropyrancarboxylic acid (VII) to 2-methoxycarbonylmethyl-6,6-dimethyl-2-tetrahydropyran carboxylic acid (I), characterised in that in stage (e) the 2-methoxycarbonylmethyl-6,6-dimethyl-2-tetrahydropyran carboxylic acid (I) is purified by means of the formation of the corresponding salt with cyclohexylamine (IA).
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