Toluene → 1-Phenylethanol, (S)-

A solution of rhodium-complex (3.4 mg, 4 μmol) obtained in Example 28 in dichloromethane degassed with argon was transferred with a syringe to the reaction vessel. Dichloromethane was evaporated in vacuo, then dry toluene (1 ml) degassed with argon, styrene (41.7 mg, 0.4 mmol) and freshly distilled catecholborane (56 μl, 0.45 mmol) were added. The reaction mixture was stirred at room temperature for 2 hrs, cooled with ice-bath, and quenched with EtOH (1 ml). 2M aqueous sodium hydroxide solution (1 ml) and 30% aqueous hydrogen peroxide (1 ml) were added. The mixture was allowed to warm up to room temperature over 30 min and then stirred for 2 hrs at this temperature. Diethyl ether (10 ml) was added to the mixture, and the orange organic layer was then washed with 1M aqueous sodium hydoxide solution and then dried over sodium sulfate. After evaporation of the solvent, the product was purified by chromatography on silica gel (pentane/diethyl ether 2:1) to give 35.7 mg of the title compound. (Yield: 73%, optical purity: 92% ee)

1. customwas transferred with a syringe to the reaction vessel
2. customDichloromethane was evaporated in vacuo
3. additionwere added
4. temperaturecooled with ice-bath
5. customquenched with EtOH (1 ml)
6. addition2M aqueous sodium hydroxide solution (1 ml) and 30% aqueous hydrogen peroxide (1 ml) were added
7. temperatureto warm up to room temperature over 30 min
8. stirringstirred for 2 hrs at this temperature
9. additionDiethyl ether (10 ml) was added to the mixture
10. washthe orange organic layer was then washed with 1M aqueous sodium hydoxide solution
11. dry with materialdried over sodium sulfate
12. customAfter evaporation of the solvent
13. customthe product was purified by chromatography on silica gel (pentane/diethyl ether 2:1)

ORD record

ord-dde023a1d7da4361aaf8f21d1d21de34

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07790882B2