(6Z,9Z)-18-bromooctadeca-6,9-diene → HCID 86678086, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of Mg (165 mg, 6.77 mmol) in THF (1 mL) was treated with a solution of linoleyl bromide (2.03 g, 6.15 mmol) in THF (1.5 mL) in one portion. The suspension was heated (45° C.) and stirred (4 h). The newly generated Grignard was then treated with a solution of (11Z,14Z)-3-((tert-butyldimethylsilyl)oxy)icosa-11,14-dienal (5) (2.0 g, 4.73 mmol) in THF (8 mL) and stirred (2 h). The reaction mixture was quenched by the addition of H2O, extracted with ether, washed with brine, dried (Na2SO4), filtered and concentrated. The crude material was subjected to chromatography (2%→3% EtOAc-hexanes) to yield (6Z,9Z,29Z,32Z)-21-((tert-butyldimethylsilyl)oxy)octatriaconta-6,9,29,32-tetraen-19-ol (6)(2.44 g, 77%) as a pale yellow oil. Rf 0.59 (10% EtOAc-hexanes), FW 673.22, C44H84O2Si.

Provenance & Evidence