2-Chloropropane → 4-ISOPROPYLFURAN-2-CARBALDEHYDE

To a suspension containing aluminium chloride (24 g, 180 mmol) in 100 mL of CS2 was added 2-furaldehyde (9.8 mL, 156 mmol). To this mixture was added dropwise isopropyl chloride (14.3 mL, 156 mmol), and the resulting mixture stirred at rt for 24 h. The dark mixture was carefully poured into a vigorously stirred 250 g of ice, and then extracted with ether (5×100 mL). The combined organic layers were washed with water, brine, dried (Na2SO4), filtered through a pad of silica gel, and concentrated. The residue was purified by flash chromatography (0-5% EtOAc in heptane) to give 4-isopropylfuran-2-carbaldehyde as an orange oil: Yield 3.5 g (16%). 1H NMR (400 MHz, CDCl3) δ ppm 1.25 (d, J=6.88 Hz, 6H), 2.80-2.91 (m, 1H), 7.16-7.18 (m, 1H), 7.47 (q, J=0.91 Hz, 1H), 9.61 (d, J=0.59 Hz, 1H).

1. extractionextracted with ether (5×100 mL)
2. washThe combined organic layers were washed with water, brine
3. dry with materialdried (Na2SO4)
4. filtrationfiltered through a pad of silica gel
5. concentrationconcentrated
6. customThe residue was purified by flash chromatography (0-5% EtOAc in heptane)

ORD record

ord-f8447c41b962472ea717289da12d6718

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07884124B2