2-Cyclohepten-1-one → HCID 69221081, compound

Temperature

0 °C

To a clear solution of 2-cyclohepten-1-one (5 g, 45.5 mmol) in ether (50 mL), cooled to 0° C., was added n-BuLi (2.0 M in hexanes, 25 mL, 50.0 mmol) dropwise to produce an opaque yellow solution. The reaction stirred for 2 h at 0° C. and then warmed to room temperature. After 1 h, the reaction was complete as determined by TLC, and quenched in 50 mL NH4Cl. The organic layer was separated and the aqueous layer was extracted with 50 mL of ether (3×). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The resulting residue was purified by flash chromatography (10% Et2O/pentane) to afford the title compound as a light yellow oil (2 g, 26% yield). IR (film) 3377, 3015, 2930, 2860, 1456, 1378, 1335, 1223, 1121, 1103, 1043, 997 cm−1; 1H NMR (300 MHz, CDCl3) δ 5.69 (tt, 1H, J=5.6, 11.9 Hz, CCH═CH), 5.59 (d, 1H, J=11.9 Hz, CCH═CH), 2.17-2.09 (m, 2H), 1.84-1.45 (m, 9H), 1.38-1.27 (m, 4H), 0.93-0.88 (m, 3H); 13C NMR (75 MHz, CDCl3) δ 139.1, 130.0, 76.1, 41.1, 38.5, 27.6, 27.5, 25.6, 24.1, 23.2, 14.1; HRMS (EI+) exact mass calculated for [M]+ (C11H20O) requires m/z 168.1514, found m/z 168.1516.

1. customto produce an opaque yellow solution
2. temperaturewarmed to room temperature
3. waitAfter 1 h
4. customquenched in 50 mL NH4Cl
5. customThe organic layer was separated
6. extractionthe aqueous layer was extracted with 50 mL of ether (3×)
7. dry with materialThe combined organic layers were dried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe resulting residue was purified by flash chromatography (10% Et2O/pentane)

ORD record

ord-5084351581ff4b969fa068b908c7ac24

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07323604B2