Triphenylphosphine → Methyl 2-[4-(2-(2,4-dichlorophenyl)ethoxy)phenylthio]isobutyrate

Participants

Reaction Steps

The title product was prepared according to the procedure described in Method B starting from methyl 2-(4-hydroxyphenylthio)iso-butyrate (prepared as described in example 3) (0.280 g, 1.24 mmol) and DIAD (0.325 g, 1.61 mmol) dissolved in 3 mL of anhydrous THF and added dropwise to a solution of 2,4-dichlorophenetylalcohol (0.260 g, 1.36 mmol) and triphenylphosphine (0.422 g, 1.61 mmol) in 4 mL of anhydrous THF at 0° C. The reaction was left overnight under magnetic stirring at room temperature After this period, the solvent was evaporated and the residue purified by silica gel chromatography using hexane/AcOEt 9.6/0.4 as eluent. 0.346 g of product were obtained (yield: 70%); Mp: 73-74° C.; TLC: silica gel, eluent hexane/AcOEt 9/1, Fr: 0.26; 1H NMR (CDCl3, 300 MHz) δ: 7.35 (m, 3H), 7.22 (m, 2H), 6.83 (d, 2H), 4.18 (t, 2H), 3.65 (s, 3H), 3.20 (t, 2H), 1.45 (s, 6H); HPLC: Column: Inertisil ODS—3 (5 μm) 4.6×250 mm, T: room temperature, mobile phase CH3CN/H2O. 85/15 (v/v), pH: as is, flow rate: 1 mL/min, 205 nm UV detector, retention time 12.58 min; KF: 0.4% H2O; E.A. conforming for C19H20Cl2O3S.

Provenance & Evidence