4-Pentenoyl chloride → Nona-1,8-dien-5-one

Temperature

-78 °C

In an oven-dried 500 mL round-bottomed flask (t=g) was added 4-Pentenoyl chloride (6.04 mL, 54.7 mmol) in THF (80 mL) to give a tan solution. After cooling to −78° C., 3-Butenylmagnesium bromide (115 mL, 57.5 mmol) was added via syringe over 90 min. After warming to room temperature for 3 hours, the reaction was quenched with saturated NH4Cl solution. THF was stripped off and the remaining was extracted with EtOAc. The organic layer was washed with brine, dried with Na2SO4, and concentrated to a slightly yellow oil. Purification (two batches) by FCC up to 40% Et2O/hexane afforded the product as a colorless oil: (5.13 g, 68%). 1H NMR (400 MHz, CDCl3) δ 5.84-5.68 (m, 2H), 5.05-4.90 (m, 4H), 2.49 (t, J=7.4 Hz, 4H), 2.35-2.20 (m, 4H).

1. customto give a tan solution
2. temperatureAfter warming to room temperature for 3 hours
3. customthe reaction was quenched with saturated NH4Cl solution
4. extractionthe remaining was extracted with EtOAc
5. washThe organic layer was washed with brine
6. dry with materialdried with Na2SO4
7. concentrationconcentrated to a slightly yellow oil
8. customPurification (two batches) by FCC up to 40% Et2O/hexane

ORD record

ord-68018d055201485085e448bff8c5e36c

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08044043B2