Iodoethane → 5-[(E)-(3-methoxy-3-oxo-1-propenyl)]-2-ethoxytoluene

Participants

Reaction Steps

In a 250 mL RBF was charged 2-ethoxy-5-iodotoluene (5 g, 19.1 mmol, prepared from 2-hydroxy-5-iodotoluene by reacting with ethyl iodide in acetone in the presence of K2CO3), methyl acrylate (17 mL), P(o-tolyl)3 (1.16 g), DMF (25 mL) and TEA (25 mL). The mixture was degased under nitrogen. To the solution was added Pd(OAc)2 (0.43 g) and the mixture was heated to reflux under nitrogen for 20 hours. After cooling to room temperature, the reaction mixture was diluted with water (200 mL) and extracted with ether (2×250 mL). The ether extracts were washed with water and brine, dried over magnesium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography. Eluting with 5-20% ethyl acetate in hexanes afforded the desired product 11 (3.3 g).

Provenance & Evidence