Octanal → HCID 10103696, compound

To a solution of 1.2 mL (7.8 mmol) of octanal in 30 mL of ether was added 15.6 mL of a 1.0 M solution of allylmagnesium bromide in ether. The reaction was allowed to stir at room temperature for 18 h and then quenched with saturated NH4Cl. The product was extracted with ether (2×20 mL), dried over Na2SO4 and filtered. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography to give 0.79 g (60%) of the allylic alcohol. 1H NMR (400 MHz, CDCl3) δ 5.80-5.70 (m, 1H), 5.04-4.99 (m, 2H), 3.53 (m, 1H), 2.52 (br s, 1H), 2.20-2.05 (m, 2H), 1.381-34 (m, 2H), 1.25-1.15 (m, 10H), 0.80 (t, J=7.1 Hz, 3H); 13C NMR (400 MHz, CDCl3) δ 133.6, 116.3, 70.6, 42.5, 37.5, 32.7, 30.6, 30.2, 26.7, 23.7, 15.2.

1. customquenched with saturated NH4Cl
2. extractionThe product was extracted with ether (2×20 mL)
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. customThe solvent was removed under reduced pressure
6. customthe remaining residue was purified by flash chromatography

ORD record

ord-c55eb9becaf043f7980c37db62da96d8

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08816095B2