Diethyl Ether → HCID 10443626, compound

Temperature

-60 °C

To a cooled and stirred ether (700 ml) solution of the (E)-5-methyl-4-tetradecenenitrile (4) (30.0 g, 136 mmols), an n-hexane solution of DIBAL-H (1.7 M, 123 ml, 209 mmols) was added dropwise at −60° C. under an argon gas. The mixture was stirred for 1 hour at −60° C. and for 3 hours at room temperature. The excess reagent was quenched with the addition of HCO2Et (5 ml). After 30 minutes of stirring, the mixture was poured into a saturated aqueous solution of NH4Cl (1.5 L). The resulting mixture was stirred for 20 minutes, acidified with a 20% aqueous solution (1 L) of H2SO4, and extracted with ether. The ether solution was washed with water, dried (MgSO4), and concentrated in a vacuum. The oily residue was subjected to chromatography on Florisil (450 g), and eluted with n-hexane-ether (50:1) to obtain 29.0 g (95.4%) of (E)-5-methyl-4-tetradecenal (5).

1. temperatureTo a cooled
2. customThe excess reagent was quenched with the addition of HCO2Et (5 ml)
3. stirringAfter 30 minutes of stirring
4. additionthe mixture was poured into a saturated aqueous solution of NH4Cl (1.5 L)
5. stirringThe resulting mixture was stirred for 20 minutes
6. extractionextracted with ether
7. washThe ether solution was washed with water
8. dry with materialdried (MgSO4)
9. concentrationconcentrated in a vacuum
10. washeluted with n-hexane-ether (50:1)

ORD record

ord-a945869f2d0344f7860ab0e7a45639aa

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06835846B2