tert-Butyl hydroperoxide → (2R-trans)-3-butyloxiranemethanol

Temperature

-60 °C

Under argon atmosphere, to anhydrous dichloromethane suspension (150 ml) containing 3.4 g of Molecular Sieves 4A were added 3.3 g (14.08 mmol) of diisopropyl D-(−)-tartarate, 3.3 g (11.73 mmol) of titanium tetraisopropoxide and 13.4 g (117.30 mmol) of (trans)-2-heptene-1-ol at −30 to −40° C. and the mixture was stirred for 10 minutes. The reaction mixture was cooled to −60° C., and under stirring, 105 ml of a toluene solution containing 2.23M of t-butylhydroperoxide was added dropwise to the mixture over 20 minutes, and the temperature of the resulting mixture was returned to room temperature over 2 hours. After completion of the reaction, the reaction mixture was added to an aqueous solution (400 ml) containing iron (III) sulfate heptahydrate (80 g) and L-tartaric acid (40 g), and the resulting mixture was extracted with dichloromethane (400 ml). The organic layer was washed with a saturated NaCl solution, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. To the residue were added ether (400 ml) and 1N-sodium hydroxide (200 ml), and the mixture was stirred at room temperature for one hour. After completion of the reaction, the organic layer was separated, and the aqueous layer was extracted with ether (50 ml). The organic layer was washed with a saturated NaCl solution, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was evaporated under reduced pressure to obtain 11.6 g (Yield: 76.2%) of the title compound.

1. stirringunder stirring
2. additionwas added dropwise to the mixture over 20 minutes
3. waitthe temperature of the resulting mixture was returned to room temperature over 2 hours
4. customAfter completion of the reaction
5. extractionthe resulting mixture was extracted with dichloromethane (400 ml)
6. washThe organic layer was washed with a saturated NaCl solution
7. dry with materialdried over anhydrous sodium sulfate
8. customthe solvent was removed under reduced pressure
9. additionTo the residue were added ether (400 ml) and 1N-sodium hydroxide (200 ml)
10. stirringthe mixture was stirred at room temperature for one hour
11. customAfter completion of the reaction
12. customthe organic layer was separated
13. extractionthe aqueous layer was extracted with ether (50 ml)
14. washThe organic layer was washed with a saturated NaCl solution
15. dry with materialdried over anhydrous sodium sulfate
16. customthe solvent was removed under reduced pressure
17. customThe residue was evaporated under reduced pressure

ORD record

ord-e8d2eda2227e4c759ec7fd38416e6006

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07326799B2