Methyl 5-formyl-2-methylfuran-3-carboxylate → 5-(1-Hydroxy-ethyl)-2-methyl-furan-3-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

Methylmagnesium bromide (370.5 ml, 1.4M in THF) is added over 30 minutes to a solution of 5-formyl-2-methyl-furan-3-carboxylic acid methyl ester (87.2 g) in THF (1200 ml) under nitrogen at 0° C. After 1 hour at 0° C., the reaction is quenched with a saturated aqueous solution of NH4Cl in water. The mixture is stirred 1 hour at 0° C. and then is extracted three times with ethyl acetate. The organic phases are combined, dried over Na2SO4 and concentrated in verve to yield 5-(1-hydroxy-ethyl)-2-methyl-furan-3-carboxylic acid methyl ester (94.5 g) as a yellow solid. The crude product obtained is used without further purification. MS (HPLC/MS): 185 (MH+).

Provenance & Evidence