Tetrahydrofuran → 4-Phenyl-2-butanol

Temperature

60 °C

A dry Schlenk tube under argon was charged with 48 mg (0.15 mmol) of neodymium (III) isopropoxide. Triethoxysilane (1.4 mL, 7.5 mmol) was added, and the reaction mixture was heated to 60° C. After 0.5 hours, 4-phenyl-2-butanone (450 μL, 3 mmol) was added. After 24 hours, the reaction was complete, as determined by GLC analysis of a aliquot taken from the reaction mixture. THF (8 mL) and aqueous NaOH (1 N, 15 mL) were added, and the mixture was stirred vigorously for 12 hours. The mixture was added to water and ether (50 mL of each), shaken vigorously, and separated. The aqueous layer was then extracted with an additional 50 mL of ether, and the combined organic layers were dried over MgSO4. After removal of the drying agent by filtration and concentration of the solution by rotary evaporation, the crude material was purified by flash chromatography (ether:hexane=3:7) to afford 245 mg (54% yield) of 4-phenyl-2-butanol (>95% pure by 1H-NMR analysis).

1. waitAfter 24 hours
2. stirringshaken vigorously
3. customseparated
4. extractionThe aqueous layer was then extracted with an additional 50 mL of ether
5. dry with materialthe combined organic layers were dried over MgSO4
6. customAfter removal of the drying agent
7. filtrationby filtration and concentration of the solution
8. customby rotary evaporation
9. customthe crude material was purified by flash chromatography (ether:hexane=3:7)

ORD record

ord-1511e1401af94ae794918aab663009db

Source dataset

uspto-grants-1993_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05220020