Ammonium Chloride → 1-Bromo-3-(4-methoxy-but-1-enyl)-benzene

To a stirred solution of NaHMDS (9.02 g, 49.2 mmol) in THF (50 mL) under nitrogen atmosphere is added drop wise at 0° C. a THF solution (50 mL) of the title A compound, (3-methoxy-propyl)-triphenyl-phosphonium bromide (20.4 g, 49.2 mmol). The resulting mixture is stirred for 1 h at 0° C. before the addition of a THF solution (50 mL) of m-bromobenzaldehyde (7 g, 37.8 mmol). The reaction mixture is further stirred for 2 h at room temperature and poured into a saturated NH4Cl aqueous solution, the aqueous layer is extracted twice with EtOAc. The combined organic extracts are dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is taken up into ether and the triphenylphosphine oxide precipitate is filtered off through a pad of celite. The filtrate is concentrate and the residual material purified by flash column chromatography on silica gel (hexane/EtOAc 95/5) to afford the title compound (as a mixture Z and E stereoisomers) as a yellow oil: Rt (HPLC, Nucleosil C18, 10:90-100:0 CH3CN/H2O+0.1% TFA within 5 min, then 100% CH3CN+0.1% TFA): 6.30 min.

1. extractionthe aqueous layer is extracted twice with EtOAc
2. dry with materialThe combined organic extracts are dried over anhydrous magnesium sulfate
3. concentrationconcentrated under reduced pressure
4. filtrationthe triphenylphosphine oxide precipitate is filtered off through a pad of celite
5. concentrationThe filtrate is concentrate
6. customthe residual material purified by flash column chromatography on silica gel (hexane/EtOAc 95/5)

ORD record

ord-fdb074f38b774f9cb222c2072a359314

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08362040B2