Cyclododeca-4,8-diene-1-carbaldehyde → 1-(4,8-Cyclododecadienyl)-2-methyl-1-propanol

Participants

Reaction Steps

4,8-Cyclododecadiene carboxaldehyde (QRM 2185) [14.0 g; 0.072 mol] was dissolved in THF (50 ml), and isopropylmagnesium chloride [36 ml; 2.0 M in Et2O, 0.072 mol] was added dropwise with stirring under N2. The reaction mixture was stirred for 30 minutes, most solvent was removed in vacuo, and the residue quenched with saturated ammonium chloride solution, then partitioned (Et2O/H2O). The organic layer was separated, washed and dried over MgSO4. The solvent was removed in vacuo, and the residue was chromatographed [silica: Et2O 50%, hexane 50%] to give 1-(4,8-cyclododecadienyl)-2-methyl-1-propanol (11.1 g, 65%) as a colourless oil.

Provenance & Evidence