Water → HCID 86706919, Verbindung

Temperatur

0 °C

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.

1. custom(˜10 min)
2. additionWhen the addition
3. temperaturethe dark brown solution was heated
4. temperatureto reflux for 1 h
5. concentrationbefore concentrating it to ˜10-20 mL under vacuum
6. dissolutionThen, the cyclic sulfite was dissolved in DCM (80 mL)
7. customThe biphasic reaction
8. washthe product was sequentially washed with water
9. dry with materialThe organic layer was dried over Na2SO4
10. filtrationfiltered through a pad of silica gel (the pad
11. washwas rinsed with diethyl ether) and
12. concentrationconcentrated under vacuum
13. customThe turbid liquid was used in the next step without purification

ORD-Eintrag

ord-f248fbd67cc34d1ea29180df3ba11c18

Quelldatensatz

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09249161B2