Water → HCID 86706919, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of crude (R)-3-methoxypropane-1,2-diol (7.66 g, 72.2 mmol) in DCM (100 mL) was slowly (˜10 min) added thionyl chloride (6.32 mL, 87 mmol) at rt. When the addition was completed, the dark brown solution was heated to reflux for 1 h before concentrating it to ˜10-20 mL under vacuum. Then, the cyclic sulfite was dissolved in DCM (80 mL) and acetonitrile (80 mL) and cooled to 0° C. Ruthenium(III) chloride (0.075 g, 0.361 mmol) and sodium periodate (23.16 g, 108 mmol) were added followed by water (100 mL). The biphasic reaction was vigorously stirred at 0° C. for 1 h. The reaction was finally diluted with diethyl ether (600 mL) and the product was sequentially washed with water, a saturated solution of sodium bicarbonate (repeated twice) and brine. The organic layer was dried over Na2SO4, filtered through a pad of silica gel (the pad was rinsed with diethyl ether) and concentrated under vacuum. The turbid liquid was used in the next step without purification.

Provenance & Evidence