2-Heptanone → 3-(Chloromethyl)cyclohexanone

Temperature

82 °C

The title compound was prepared following the procedure described in (N. Di Bello et al., Synthesis, 1978, 227. To a solution of bicycle[4.1.0]heptan-2-one (13.8 g, 125 mmol) in acetonitrile (300 mL) was added pyridine hydrochloride (43.3 g, 375 mmol) which had been triturated with Et2O and dried under high vacuum. The solution was stirred under N2 at 82° C., overnight. The reaction mixture was partially concentrated, poured into brine (200 mL) and extracted with Et2O (4×100 mL). The ether extracts were combined, washed with brine (100 mL), dried and concentrated. The residual oil was purified on a Biotage flash chromatography system (15% ethyl acetate in hexanes) to yield the title compound (13.4 g, 91 mmol, 73.1% yield) as an oil. LCMS: 147.09 (M+H), 149.10 (M+3, 30% rel. intensity). 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 1.51-1.60 (m, 1 H) 1.62-1.74 (m, 1 H) 1.95-2.02 (m, 1 H) 2.06-2.13 (m, J=13.47, 9.80, 3.62, 3.62 Hz, 1 H) 2.13-2.20 (m, 1 H) 2.20-2.31 (m, 2 H) 2.35-2.43 (m, 1 H) 2.45-2.51 (m, 1 H) 3.45-3.55 (m, 2 H). 13C NMR (126 MHz, CHLOROFORM-d) δ ppm 24.63, 28.75, 40.85, 41.15, 45.39, 210.25.

1. customThe title compound was prepared
2. customDi Bello et al., Synthesis, 1978, 227
3. customhad been triturated with Et2O
4. customdried under high vacuum
5. concentrationThe reaction mixture was partially concentrated
6. additionpoured into brine (200 mL)
7. extractionextracted with Et2O (4×100 mL)
8. washwashed with brine (100 mL)
9. customdried
10. concentrationconcentrated
11. customThe residual oil was purified on a Biotage flash chromatography system (15% ethyl acetate in hexanes)

ORD record

ord-0b825f7dd66049fe849ea4ebd922ca16

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129398B2