Salicylaldehyde → 2H-1-Benzopyran-3-carbonitrile

Temperature

90 °C

A microwave vessel was charged with 2-hydroxybenzaldehyde (Aldrich, 3.0 mL, 28.6 mmol), acrylonitrile (9.4 mL, 143 mmol) and 1,4-diazabicyclo[2.2.2]octane (0.80 g, 7.2 mmol), and heated in a microwave Personal Chemistry at 90° C. for 13 hours. Sodium hydroxide (1N, 200 mL) was added and the mixture was extracted twice with ethyl acetate (200 mL), and the combined organic layer washed with brine, dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was chromatographed on silica gel eluting with 0-to-20% ethyl acetate in hexane providing the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 4.88 (d, J=1.36 Hz, 2H), 6.90 (d, J=8.14 Hz, 1H), 7.01 (td, J=7.46, 1.01 Hz, 1H), 7.30 (m, 2H), 7.58 (s, 1H). MS (DCI) m/z 175.05 (M+NH4)+.

1. extractionthe mixture was extracted twice with ethyl acetate (200 mL)
2. washthe combined organic layer washed with brine
3. dry with materialdried with anhydrous sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. customThe residue was chromatographed on silica gel eluting with 0-to-20% ethyl acetate in hexane providing the title compound

ORD record

ord-5073ca04f2204a5f854730bcc01a30fb

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08350083B2