2-Bromopropane → HCID 54298051, compound

Participants

Reaction Steps

To a mixture of ether (344 ml) and 2,6,10,14,18-pentamethyl-5,9,13,17-nonadecatetraenal (34.4 g), Grignard reagent (prepared by adding portionwise isopropyl bromide (18.5 g) to a mixture of ether (100 ml) and metallic magnesium (3.7 g), adding further t-butyl acetate (17.4 g) thereto while cooling with ice and then stirring the resultant mixture for 1 hour) is dropwise added while cooling with ice. The resultant mixture is stirred at room temperature for 3 hours, and the reaction mixture is poured into an aqueous saturated solution of ammonium chloride. The ether layer is separated, washed with water, dried and evaporated. The residual material is chromatographed on silica gel (500 g) using a mixture of benzene and ethyl acetate (9.5:0.5 by weight) to give ethyl 3,7,11,15,19-pentamethyl-6,10,14,18-eicosatetraen-2-ol-1-carboxylate (28.5 g) as a pale yellow oil. IR: 3480, 1030 cm-1 (OH); 1720, 1180 cm-1 (COO).

Provenance & Evidence