Dimethylformamide → (10Z,13Z)-nonadeca-10,13-dienal

A 100 mL round bottom flask charged with magnesium turnings (462 mg, 19.0 mmol) and a stir bar was dried with a high temperature heat gun for 5 minutes. The flask was cooled to room temperature under nitrogen then charged with THF (25 mL). Linoleyl bromide (1.9 g, 5.76 mmol) was added drop wise and the solution was heated to 45° C. for 3 hours under nitrogen. Upon completion, DMF (1.3 mL, 16.7 mmol) was added slowly and the solution was stirred for 1 hour at room temperature. The solution was diluted with ether (75 mL) and washed with 5% HCl (3×50 mL). The ether solution was dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography (column: 2″×10″; eluted with 2% ether/hexanes) to afford the title compound as a colorless oil (3.5 g, 83%).

1. customwas dried with a high temperature
2. temperatureheat gun for 5 minutes
3. additionthen charged with THF (25 mL)
4. temperaturethe solution was heated to 45° C. for 3 hours under nitrogen
5. washwashed with 5% HCl (3×50 mL)
6. dry with materialThe ether solution was dried on magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo to dryness
9. customThe residue was purified by column chromatography (column
10. washeluted with 2% ether/hexanes)

ORD record

ord-281f638d2611415e9318ceb4eab96918

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08865675B2