Ethyl Acetate → 4-(Propane-1-sulfonyl)-benzaldehyde

Participants

Reaction Conditions

Reaction Steps

4-Fluorobenzaldehyde (3.03 mL, 28.2 mmol) and sodium n-propylsulphinate (4.03 g, 31.0 mmol, synthesised as described in J. Med. Chem. 1989, 32, 2436) were dissolved in dry DMSO and the resulting solution heated at 100° C. for 18 h. The mixture was allowed to cool and then poured onto approximately 50 g of ice. After the ice had melted, the product was extracted into ethyl acetate (×2). The combined organic extracts were dried (MgSO4) and concentrated. Chromatography on silica eluting with 20 to 40% ethyl acetate in hexane afforded the product as a white solid (3.21 g, 54% yield). 1H NMR (400 MHz, CDCl3) 1.02 (3H, t, J=7.5 Hz), 1.72-1.82 (2H, m), 3.10-3.14 (2H, m), 8.07-8.11 (4H, m), 10.14 (1H, s).

Provenance & Evidence