Diethyl Ether → 1-Butanone, 1-(4-pyridyl)-

Pyridinium chlorochromate (4.27 g, 19.84 mmol) was suspended in dry dichloromethane (50 ml) in a round-bottom flask under an atmosphere of N2. After stirring for 5 min, 1-(4-pyridyl)-1-butanol (2.0 g, 13.23 mmol) in dry dichloromethane (10 ml) was added. The reaction was followed by t.l.c. and once complete (˜2 h) anhydrous ether (70 ml) was added. The supernatant was decanted and the residual black gum was washed with anhydrous ether (4×100 ml). The combined organic fractions were concentrated in vacuo, and the black tar-like substance was purified by flash chromatography [EtOAc as eluant] to give a brown oil. The product was then purified by silica gel column chromatography [3:1 EtOAc:hexanes as eluant] to give n-propyl 4-pyridyl ketone [Registry No. 1701-71-9] as a yellowy-green oil (520 mg, 27%). 1H NMR (300 MHz, CDC3): δ 1.01 (3H, t, J=7.5 Hz, CH3), 1.78 (2H, sxt, J=7.4 Hz, —CH2—), 2.95 (2H, t, J=7.2 Hz, CH2—CO), 7.72 (2H, d, J=5 Hz, H-3, H-5), 8.81 (2H, d, J=5 Hz, H-2, H-6) ppm.

1. customThe supernatant was decanted
2. washthe residual black gum was washed with anhydrous ether (4×100 ml)
3. concentrationThe combined organic fractions were concentrated in vacuo
4. customthe black tar-like substance was purified by flash chromatography [EtOAc as eluant]
5. customto give a brown oil
6. customThe product was then purified by silica gel column chromatography [3:1 EtOAc:hexanes as eluant]

ORD record

ord-57e6e44cf1184871b77216b0939406dd

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962003B2