Hydrochloric Acid → HCID 21281102, compound

Temperature

-78 °C

Under a nitrogen atmosphere 13.7 mL of a 2.6M solution of n-butyllithium in n-hexane was added to a cold (-78° C.) stirred solution of 5.2 grams (0.0325 mole) of 2-phenylthiophene in 61 mL of tetrahydrofuran. This mixture was stirred at -78° C. for 1.5 hours. To this cold mixture was added 2-phenylpropionaldehyde (4.6 gram, 0.0336 mole), and the mixture was stirred for 15 minutes. The mixture was allowed to warm to room temperature and stir for two days. The mixture was cooled to 0° C., and approximately 45 mL of 1.2 N hydrochloric acid was added. The organic phase was separated from the aqueous phase and the aqueous phase, was extracted with chloroform. The chloroform extract was combined with the organic phase and washed with an aqueous, ammonium chloride solution. The washed organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure leaving a residue. This residue was purified by column chromatography on silica gel, eluting with ethyl acetate:n-hexane (10:90), to yield 9.2 g of 2-phenyl-1-(5-phenylthien-2-yl)-1-propanol as an oil.

1. stirringthe mixture was stirred for 15 minutes
2. temperatureto warm to room temperature
3. stirringstir for two days
4. temperatureThe mixture was cooled to 0° C.
5. customThe organic phase was separated from the aqueous phase
6. extractionthe aqueous phase, was extracted with chloroform
7. extractionThe chloroform extract
8. washwashed with an aqueous, ammonium chloride solution
9. dry with materialThe washed organic phase was dried over anhydrous magnesium sulfate
10. filtrationfiltered
11. customThe filtrate was evaporated under reduced pressure
12. customleaving a residue
13. customThis residue was purified by column chromatography on silica gel
14. washeluting with ethyl acetate:n-hexane (10:90)

ORD record

ord-65332a5d86324a0eb6868fde2b432806

Source dataset

uspto-grants-1988_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04792567