HCID 69221081, compound → 3-Butylcyclohept-2-en-1-one

To a solution of (Z)-1-butylcyclohept-2-enol (2 g, 11.9 mmol) dissolved in dichloromethane (60 mL) was pyridine chlorochromate on basic alumina (20 wt. %, 25.7 g, 23.8 mmol). The resulting reddish solution was stirred at room temperature for 2 h until determined to be complete by TLC. The mixture was diluted in 100 mL diethyl ether and stirred for 1 h after which it was poured over filter paper that was subsequently washed with the ether. The filtrate was partially concentrated (30 mL) and passed through a Florisil column with ether (100 mL). The resulting colorless solution was concentrated and purified by flash chromatography (5% Et2O/Pentane) to provide a colorless oil (920 mg, 47% yield). IR (film) 3477, 2933, 2864, 1662, 1458, 1421, 1375, 1344, 1322, 1267, 1201, 1124, 1103, 1048, 937, 875, 855 cm−1; 1H NMR (300 MHz, CDCl3) δ 5.89 (s, 1H, COCH), 2.58-2.53 (m, 2H, COCH2), 2.41-2.38 (m, 2H, HC═CCH2), 2.18 (t, 2H, J=6.91 Hz, HC═CCH2(CH2)2CH3), 1.80-1.74 (m, 2H, COCH2CH2), 1.50-1.40 (m, 2H, HC═CCH2CH2), 1.38-1.25 (m, 2H, HC═C(CH2)2CH2CH3), 0.90 (t, 3H, J=7.18 Hz, CH2CH3); 13C NMR (75 MHz, CDCl3) δ 204.4, 162.4, 128.2, 42.1, 40.8, 32.5, 29.7, 25.1, 22.4, 21.2, 13.9; HRMS (EI+) exact mass calculated for [M]+ (C11H18O) requires m/z 166.1358, found m/z 166.1359.

1. stirringstirred for 1 h after which it
2. additionwas poured
3. filtrationover filter paper that
4. washwas subsequently washed with the ether
5. concentrationThe filtrate was partially concentrated (30 mL)
6. concentrationThe resulting colorless solution was concentrated
7. custompurified by flash chromatography (5% Et2O/Pentane)

ORD record

ord-14b80b716da0467a8c9aee123089db7f

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07323604B2