2,6-Lutidine → HCID 59283874, compound

Participants

Reaction Steps

A solution of methyl 4-(tert-butyldimethylsilyloxy)-3-allyl-5-methylbenzoate (0.239 g, 0.742 mmol) in dioxane/water (3:1, 16 mL) was treated with 2,6-lutidine (173 uL, 1.484 mmol), osmium tetroxide (3.8 mg, 0.0148 mmol) which was added as solution in acetone (1 mL) followed by sodium periodate (635 mg, 2.97 mmol). The reaction was stirred at room temperature under a nitrogen atmosphere. After 2 hours, TLC analysis showed mostly product. the reaction was then diluted with ethyl acetate (20 mL) and water (10 mL). The ethyl acetate layer was separated and the aqueous layer was extracted once more with ethyl acetate (10 mL). The combined ethyl acetate extracts were washed with brine. They were then dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. A brown oil (0.255 g) was recovered. The very unstable aldehyde was then reduced immediately by first dissolving it in methanol (5 mL) and after cooling in an ice-bath, adding sodium borohydride (50 mg, 2 equivalents). This reaction was stirred in the ice-bath and after 10 minutes TLC analysis indicated complete conversion to the alcohol. The reaction was then quenched with acetone (2 mL) and stirred for 10 minutes. The reaction mixture was then evaporated to dryness and the residue was dissolved in ethyl acetate (30 mL) and then washed once with saturated aqueous ammonium chloride and then saturated aqueous sodium bicarbonate. The ethyl acetate solution was then dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. A dark brown viscous oil was recovered which was purified by preparative TLC on silica using 25% ethyl acetate.hexanes. The product was obtained as a clear, viscous oil. Yield 138 mg (58%).

Provenance & Evidence