Potassium t-amylate → Naphthalene

Participants

Reaction Conditions

Reaction Steps

To the suspension of ethyl triphenyl phosphonium bromide (3.72 g, 10.0 mmol) in anhydrous THF (8 ml), a solution is added by drops of potassium tert-amylate (5.5 ml, 9.3 mmol, 1.7 M solution in toluene) using a syringe at room temperature. After 1 hour, the reaction mixture is cooled to a temperature of 0° C., a solution is added of aldehyde with formula 20 (1.68 g, 7.16 mmol), the cooling bath is removed, and mixing is carried out for 3 hours at room temperature. Then, the reaction mixture is diluted with cyclohexane (30 ml), the sediment is filtered off, and the solvent is evaporated at reduced pressure. The residue is chromatographed on silica gel (cyclohexane), obtaining a naphthalene derivative with formula 21 in the form of an oil as a mixture of isomers E:Z=1.82:1 (1.66 g, 94%).

Provenance & Evidence