Iodine → HCID 86594933, compound

Participants

Reaction Steps

Magnesium turnings (4.2 g) were suspended in diethyl ether (45 mL) and then initiated with a crystal of I2. 1-Bromo-2-methylpropane (1.37 mL, 12 mmol) was then added to the magnesium suspension. The mixture turned a cloudy white after the flask was heated with α heat gun. A solution of 1-bromo-α-D-galactose tetraacetate 4 (4.307 g, 10.5 mmol) in diethyl ether (10 mL) was added dropwise into the Grignard reaction mixture. The reaction went to completion after the mixture was heated at reflux for 4 h. The mixture was slowly poured into water (300 mL). Glacial AcOH (11 mL) was added. The mixture was separated and the aqueous layer was concentrated. The residue was treated with acetic anhydride (150 ML) and pyridine (150 mL) overnight. The resulting mixture was diluted with water (300 mL), extracted with diethyl ether (3×250 mL), washed with water (2×150 mL), and dried with magnesium sulfate. The solvent was removed under reduced pressure. The product was purified by flash chromatography (silica gel, 2:3 ethyl acetate/hexane) to afford 5 as a white solid (2.80 g, 7.24 mmol, 69%).

Provenance & Evidence