Trifluoroacetic acid → HCID 58264329, compound

Participants

Reaction Steps

1,2-Dilinoleyloxy-3-allyloxypropane (25) (18 g, 28.6 mmol) was dissolved in ethanol (150 mL) in a 500 mL round bottom flask with a stir bar. Trifluoroacetic acid (15 mL) and tetrakis (triphenylphosphine) palladium(0) (5.0 g, 4.3 mmol) were added and the flask flushed with nitrogen. A water condenser was fitted and the flask wrapped tin foil to reduce exposure to light. The reaction was refluxed under nitrogen overnight. The solution was concentrated to an orange oil, then redissolved in DCM (250 mL), and washed with water (2×200 mL) and saturated brine (1×200 mL). The aqueous phases were combined and extracted with DCM (2×100 mL). Organic phases were combined, dried over MgSO4 and concentrated. The crude product was purified by column chromatography to yield 1,2-dilinoleylglycerol as a colorless oil (11.0 g, 18.7 mmol, 65.3%).

Provenance & Evidence