Diisopropylamine → HCID 86678091, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (−40° C.) solution of N,N,-di-isopropylamine (462 μL, 3.27 mmol) in THF (9 mL) was added nBuLi (1.45 mL, 3.63 mmol as a 2.5M solution in hexanes). After stirring (40 min) the solution was cooled (−78° C.) and treated with di-linoleylmethylketone (1.50 g, 2.85 mmol, neat) dropwise. After stirring (40 min) the newly generated lithium enoloate was added to a cold (−78° C.) solution of linoleyl aldehyde (804 mg, 3.04 mmol) in THF (4 mL). After stirring (1 h, −78° C.) the mixture was quenched by the addition of sat. aq. NH4Cl, then extracted with EtOAc, dried (Na2SO4), filtered and concentrated. The crude material was subjected to chromatography (0.5%→1% EtOAc-hexanes) to yield (6Z,9Z,29Z,32Z)-20-((8Z,11Z)-heptadeca-8,11-dien-1-yl)-21-hydroxyoctatriaconta-6,9,29,32-tetraen-19-one (10) (1.50 g, 62%) as a colorless oil. Rf 0.27 (5% EtOAc-hexanes), FW 791.39, C55H98O2.

Provenance & Evidence