3-Chlorobenzaldehyde → HCID 14185029, compound

To a cooled solution of 3-chlorobenzaldehyde (22.5 g, 160 mmol) in 100 mL anhydrous THF under inert nitrogen atmosphere was added slowly via syringe a 1.6 M solution of vinyl magnesium chloride in THF (100 mL, 160 mmol) and the solution stirred for three h allowing to warm to room temperature. The reaction was quenched with saturated solution of ammonium chloride and the organic layer was separated, extracted with ethyl acetate (2×200 mL), and organic layers were combined, dried over magnesium sulfate, filtered and concentrated under vacuum. Purification by Horizon MPLC with a 40M+ silica gel column using a gradient eluent of 0-40% ethyl acetate in hexane afforded the title compound (22.4 g, 44%). m/z (ES) 168, 170 (M, M+2)+, 190, 192 (MNa, MNa+2)+. 1HNMR (500 MHz, CDCl3) δ: 7.38 (s, 1H), 7.35-7.22 (m, 3H), 5.90 (ddd, J=7.3, 10.0, 17.4 Hz, 1H), 5.38 (d, J=17.5 Hz, 1H), 5.18 (d, J=7.2 Hz, 1H), 5.15 (d, J=10.1 Hz, 1H), 0.96 (s, 9H), 0.18 (s, 3H), 0.08 (s, 3H).

1. customThe reaction was quenched with saturated solution of ammonium chloride
2. customthe organic layer was separated
3. extractionextracted with ethyl acetate (2×200 mL), and organic layers
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under vacuum
7. customPurification by Horizon MPLC with a 40M+ silica gel column

ORD record

ord-58b47b2837b74cf3b6a2791325366f65

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247415B2