Toluene → (S)-3-chlorostyrene oxide

Temperature

50 °C

Into toluene (10 ml) were added (S)-2-(3-chlorophenyl)-2-(3,4,5,6-tetrahydro-[2H]-pyran-2-yloxy)ethyl methanesulfonate (3.0 g), p-toluenesulfonic acid monohydrate (1.7 g) and methanol (0.5 g), and the resulting mixture was:stirred at 50° C. for 1 hour. The reaction mixture was Washed with a saturated aqueous sodium hydrogen carbonate solution and then with a saturated aqueous sodium chloride solution. To the organic layer was added 20% NaOH (10 ml) and the resulting mixture was stirred vigorously at room temperature for 1 hour. The reaction mixture was subjected to layer separation, and the organic layer was washed with water, then with a saturated aqueous sodium chloride solution and dried with anhydrous magnesium sulfate. The desiccant was filtered off, then the solvent was distilled off, and the resulting oily substance was distilled under reduced pressure to obtain a colorless oily compound mentioned above (1.27 g, 91.7%). The optical purity of the product obtained was 99.9% e.e. as determined by HPLC.

1. washThe reaction mixture was Washed with a saturated aqueous sodium hydrogen carbonate solution
2. additionTo the organic layer was added 20% NaOH (10 ml)
3. stirringthe resulting mixture was stirred vigorously at room temperature for 1 hour
4. customThe reaction mixture was subjected to layer separation
5. washthe organic layer was washed with water
6. dry with materialwith a saturated aqueous sodium chloride solution and dried with anhydrous magnesium sulfate
7. filtrationThe desiccant was filtered off
8. distillationthe solvent was distilled off
9. distillationthe resulting oily substance was distilled under reduced pressure
10. customto obtain a colorless oily compound
11. customThe optical purity of the product obtained

ORD record

ord-ca3c1f771dfd470980f2199ba9159f1f

Source dataset

uspto-grants-2003_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06642395B1