(+)-Styrene oxide → 2-Phenyl-1-propanol, (+-)-

Temperature

-60 °C

An oven dried 500.0 mL three necked round bottom flask equipped with a mechanical stirrer, thermometer, addition funnel with a continuous nitrogen blanket is charged with 2.0 M solution of trimethylaluminum (65.6 mL, 131.2 mmol) and toluene (75.0 mL). Reaction solution was then chilled to −60° C. with dry ice/acetone bath. To this solution was then added R-styrene oxide dissolved in 100.0 mL of toluene over a period of 50.0 minutes (reaction is quite exothermic and can be controlled by the rate of addition of substrate). After stirring at this temperature for 60.0 minutes, reaction was brought to room temperature and stirred for 4.0 hours. Reverse quenched reaction at room temperature into a slurry of THF (100.0 mL) and sodium sulfate decahydrate (46.0 g) very cautiously over a period of 90.0 minutes (quenching was quite exothermic with evolution of gas). Filtered the precipitate formed over hyflo, then concentrated filtrate to provide the intermediate title compound, (2R)2-phenylpropan-1-ol, (11.03 g, 92.6%) as an oil; 1H nmr (CDCl3, 300 MHz) δ 1.28-1.29 (d, 3H, J=6.9 Hz), 1.5 (b, 1H), 2.9-3.0 (m, 1H), 3.69-3.70 (d, 2H, J=6.64 Hz), 7.24-7.35 (aromatic); 13C nmr (CDCl3, 300 MHz) δ 18.31, 43.15, 69.40, 127.38, 128.20, 129.26, 144.39.

1. dry with materialAn oven dried 500.0 mL three necked round bottom flask
2. customequipped with a mechanical stirrer
3. additionthermometer, addition funnel with a continuous nitrogen blanket
4. customReaction solution
5. customreaction
6. additioncan be controlled by the rate of addition of substrate)
7. customreaction
8. customwas brought to room temperature
9. stirringstirred for 4.0 hours
10. customReverse quenched
11. customreaction at room temperature into a slurry of THF (100.0 mL) and sodium sulfate decahydrate (46.0 g) very cautiously over a period of 90.0 minutes (
12. customquenching
13. filtrationFiltered the precipitate
14. customformed over hyflo

ORD record

ord-7b277e2877b946b181f967f8a606a82a

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06803484B2