反应详情

Tin (IV) chloride (13.6 ml, 0.116 mol) was added to an ice-bath cooled solution of 1-methyl-2-(methylthio)benzene (10 g, 0.073 mol) in anhydrous dichloromethane (200 ml) under nitrogen and stirred for a further 2 hours at 0° C. α,α-Dichloromethyl methyl ether (6.56 ml, 0.073 mol) was introduced and the reaction stirred for 1 hour at <10° C. before the cooling was removed. After attaining room temperature, the reaction mixture was poured into ice/water (400 ml), stirred and then extracted with dichloromethane (×3). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, concentrated onto silica gel and purified by flash chromatography, eluting with diethyl ether/isohexane (10:1) to yield the sub-title compound as a brown oil (6.54 g) in 54% yield.

1. additionwas introduced
2. customwas removed
3. customAfter attaining room temperature
4. additionthe reaction mixture was poured into ice/water (400 ml)
5. stirringstirred
6. extractionextracted with dichloromethane (×3)
7. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated onto silica gel
10. custompurified by flash chromatography
11. washeluting with diethyl ether/isohexane (10:1)