Formaldehyde → HCID 86685123, compound

Participants

Reaction Conditions

Reaction Steps

(2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxy-2,3-difluoro-phenyl)methyl]phenyl]-6-methoxy-tetrahydropyran-2-carbaldehyde 3j (2.4 g, 3.23 mmol) was dissolved in 20 mL 1,4-dioxane, followed by addition of 5 mL 37% formaldehyde solution and 13 mL 1 M sodium hydroxide. The reaction mixture was stirred for 21 hours at 70° C. Thereafter, the reaction mixture was extracted with ethyl acetate (50 mL×3) after 20 mL of saturated sodium chloride solution were added. The organic extract was combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxy-2,3-difluoro-phenyl)methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-carbaldehyde 3k (1.6 g, yellow grease), yield: 64.0%.

Provenance & Evidence