4-Phenyl-3-Buten-2-one → HCID 12687274, 화합물

온도

-65 °C

(S)-N-methyl-1-phenyl-2-(1-piperidinyl)ethanamine (361.1 mg, 1.66 mmol) was dissolved in ether (12 mL) and n-butyllithium (2.5M in hexanes, 0.66 mL, 1.65 mmol) was added to the solution at -65° C. The solution was stirred for 5 min at -65° C., warmed to 0° C. and stirred for 10 min at 0° C. To a second flask was added CuI (263 mg, 1.38 mmol) and 10 mL of diethyl ether. This solution was cooled to -40° C. and treated with n-butyl lithium (0.55 mL, 1.38 mmol). The solution in the first flask was cooled to -35° C. and added via canula to the solution of n-BuCu in the second flask. The resulting solution was stirred for 15 min at -35° C., for 10 min at -30° C., and cooled to -78° C. After 30 min, the ether (1 mL) solution of 4-phenyl-3-buten-2-one (201.5 mg, 1.38 mmol) was added slowly at -78° C. The reaction mixture was stirred for 1 hr at -78° C. and warmed to -20° C. The reaction was quenched by adding 4N NH4Cl (15 mL) at -20° C. and extracted with ether (20 mL). The extract was washed with 1N HCl (15 mL), dried (Na2SO4) and concentrated. The oily residue was purified by column chromatography on silica gel (8:1=hexanes/ethyl acetate) to afford (+)-4-phenyl-2-octanone (95.6 mg, 34% chemical yield, 2% ee, [α]D =0.06 (c=5.00, chloroform)).

1. temperaturewarmed to 0° C.
2. stirringstirred for 10 min at 0° C
3. temperatureThis solution was cooled to -40° C.
4. temperatureThe solution in the first flask was cooled to -35° C.
5. additionadded via canula to the solution of n-BuCu in the second flask
6. stirringThe resulting solution was stirred for 15 min at -35° C., for 10 min at -30° C.
7. temperaturecooled to -78° C
8. waitAfter 30 min
9. stirringThe reaction mixture was stirred for 1 hr at -78° C.
10. temperaturewarmed to -20° C
11. customThe reaction was quenched
12. additionby adding 4N NH4Cl (15 mL) at -20° C.
13. extractionextracted with ether (20 mL)
14. washThe extract was washed with 1N HCl (15 mL)
15. dry with materialdried (Na2SO4)
16. concentrationconcentrated
17. customThe oily residue was purified by column chromatography on silica gel (8:1=hexanes/ethyl acetate)

ORD 기록

ord-37173857d2d74262835e78231292a092

출처 데이터셋

uspto-grants-1992_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05134238