Diethyl Ether → (E)-5-(2-nonyloxyphenyl)-3-hydroxy-3-methyl-1,4-pentadiene

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(2-nonyloxyphenyl)-3-butene-2-one (58 g) in tetrahydrofuran (200 mL) was added to a solution of vinylmagnesium bromide in tetrahydrofuran (200 mL, 1.6M diluted to lL with more tetrahydrofuran) at -30° C. After complete addition, the mixture was stirred at 0° C for 30 min qquenched with saturated aqueous ammonium chloride (100 mL) and ether (2L) and filtered free of solids. Concentration of the organic extract and purification by chromatography over siica gel yielded (E)-5-(2-nonyloxyphenyl)-3-hydroxy-3-methyl-1,4-pentadiene (40 g) as an oil.

Provenance & Evidence