Sodium Hydroxide → (6-Methoxymethoxymethylpyridin-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

Compound (2) dissolved in tetrahydrofuran (100 ml) is added dropwise to a suspension of lithium aluminum hydride (9 g, 2.18×10−1 mol) in tetrahydrofuran (200 ml) cooled to −80° C. and maintained under an inert atmosphere. The reaction mixture is stirred at −80° C. for 30 minutes after the end of the addition. H2O (18 ml), 10% NaOH in water (23 ml), THF (200 ml) and then H2O (53 ml) are added. The temperature is then returned to room temperature, followed by addition of ammonium acetate (20 g, 2.6×10−1 mol) to the suspension. After 15 minutes, the reaction mixture is filtered through Celite and the filtrate is concentrated under vacuum. The residue is taken up in dichloromethane, the phases are separated by settling and the organic phase is dried over Na2SO4. After concentration under reduced pressure, the residue is purified by filtration through silica (eluent: 96/4 CH2Cl2/methanol). The product obtained (14.2 g) is used in the following step without further purification.

Provenance & Evidence