Process for the synthesis of 5-((2-methyl-1h-imidazol-1-yl)methyl)furan-2-carbaldehyde and of nitrones from 5-((2-methyl-1h-imidazol-1-yl)methyl)furan-2-carbaldehyde

A method for the preparation of a compound of formula I:

• comprising the following successive steps:
• (i) preparing a mixture comprising a carbohydrate, an alkali or alkaline-earth metal chloride, hydrochloric acid, water, and an organic solvent, the mixture being heated to a temperature within a range of from 35° C. to 90° C., the organic solvent being a water-insoluble polar aprotic solvent, and the carbohydrate being a monosaccharide, a polysaccharide or a mixture thereof;
• (ii) cooling the mixture obtained from step (i) to give a cooled mixture, separating the cooled mixture into an aqueous phase and an organic phase, and recovering the organic phase, the organic phase comprising the organic solvent and a compound of formula II:
• (iii) mixing 2-methylimidazole and the organic phase obtained from step (ii), the 2-methylimidazole being in molar excess relative to the compound of formula II;
• and
• (iv) recovering the compound of formula I formed following step (iii).

The method according to claim 1, wherein step (i) comprises the following steps:

• (i1) preparing a composition comprising the carbohydrate, the alkali or alkaline-earth metal chloride, the hydrochloric acid, and the water;
• and
• (i2) adding the composition obtained from step (i1) to the organic solvent heated to a temperature within a range of from 35° C. to 90° C.;
• or
• (i1) adding the carbohydrate to the organic solvent heated to a temperature within a range of from 35° C. to 90° C.;
• (i2) preparing a composition comprising the alkali or alkaline-earth metal chloride, the hydrochloric acid, and the water;
• and
• (i3) adding the composition obtained from step (i2) to the heated organic solvent comprising the carbohydrate obtained from step (i1);
• or
• (i1) preparing a composition comprising the carbohydrate and the water;
• (i2) preparing a composition comprising the organic solvent, the hydrochloric acid, and the alkali or alkaline-earth metal chloride, the composition being heated to a temperature within a range of from 35° C. to 90° C.;
• and
• (i3) adding the composition obtained from step (i1) to the heated composition obtained from step (i2);
• or
• (i1) preparing a composition comprising the organic solvent, the hydrochloric acid, the alkali or alkaline-earth metal chloride, and the water, the composition being heated to a temperature within a range of from 35° C. to 90° C.;
• and
• (i2) adding the carbohydrate to the heated composition obtained from step (i1);
• or
• (i1) preparing a composition comprising the carbohydrate, the organic solvent, and the alkali or alkaline-earth metal chloride, the composition being heated to a temperature within a range of from 35° C. to 90° C.;
• and
• (i2) adding a solution of hydrochloric acid to the heated composition obtained from step (i1).