2-Methyl-4-nitrophenol → 2-Methyl-4-nitrophenyl 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranoside

Participants

Reaction Conditions

Reaction Steps

SnCl4 (0.6 ml) is added slowly to a solution of 2-methyl-4-nitrophenol (ref.: J. S. ANDERSON and K. C. BROWN, Synthetic Commun., 13, 233-236, 1983) and 1,2,3,4,6-penta-O-acetyl-β-D-galactose (1 g, 2.56 mmol), kept at room temperature. The reaction mixture is then stirred under nitrogen for 12 hours at 60° C. After hydrolysis in iced water, extraction with CH2Cl2, followed by washing with a saturated solution of sodium bicarbonate and then water, gives 42, which is then purified by chromatography on silica gel (yield=45%).

Provenance & Evidence