反应详情

温度

45 °C

A 100 mL round bottom flask, charged with magnesium turnings (355 mg, 14.6 mmol) and a stir bar, was dried with a high temperature heat gun for 5 minutes. Upon cooling under nitrogen, THF (6 mL) was added followed by linolaidyl bromide (6.02 g, 18.3 mmol). The mixture was heated to 45° C. and a single grain of iodine was added. The reaction was refluxed for 2.5 hours then cooled to room temperature where upon a solution of (10Z,13Z)-nonadeca-10,13-dienal (3.4 g, 12.4 mmol) in THF (10 mL) was added. The solution was stirred for 1.5 hours at room temperature then poured into water (150 mL) and 5% HCl (50 mL) was added. Upon dissolution of the magnesium, the solution was extracted with ether (2×150 mL). The combined ether extracts were dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography (100% hexanes) to afford the title compound as a colorless oil (4.57 g, 71%).

1. customwas dried with a high temperature
2. temperatureheat gun for 5 minutes
3. temperatureUpon cooling under nitrogen
4. additionTHF (6 mL) was added
5. temperatureThe reaction was refluxed for 2.5 hours
6. additionwas added
7. additionwas added
8. extractionthe solution was extracted with ether (2×150 mL)
9. dry with materialThe combined ether extracts were dried on magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated in vacuo to dryness
12. customThe residue was purified by column chromatography (100% hexanes)