Benzenepropanal → HCID 10059847, compound

Temperature

0 °C

Following a modified procedure of Matsuda (Matsuda, F. Et al., Chem. Eur. J. 5, 3252-3259 (1999)); n-butyllithium (1.6 M in hexanes, 8.8 ml, 14.1 mmol, 1.0 eq.) was added dropwise to a solution of ethynyltrimethylsilane (2.0 ml, 14.1 mmol, 1.0 eq.) in THF (6 ml) at −78° C. After addition, the mixture was allowed to warm slowly to 0° C. and stirred for 1 h. The mixture was cooled to −78° C. and a solution of hydrocinnamaldehyde (2.2 ml, 17.0 mmol, 1.2 eq.) in THF (3 ml) was added dropwise. The mixture was then allowed to slowly warm to −10° C. and stirred for 1 h before being quenched by the addition of saturated NH4Cl solution (10 ml) followed by EtOAc (10 ml). The aqueous layer was extracted with EtOAc (3×10 ml), the combined organic phases were washed with brine (15 ml) before being dried (MgSO4), filtered and concentrated to give the crude product. This was purified by column chromatography on silica, eluting with petrol/EtOAc (100:5), giving the title product 81 as a clear, colourless oil (3.1 g, 94%). Analytical data consistent with the literature (Matsuda, F. Et al., Chem. Eur. J. 5, 3252-3259 (1999)).

1. additionAfter addition
2. temperatureThe mixture was cooled to −78° C.
3. temperatureto slowly warm to −10° C.
4. stirringstirred for 1 h
5. custombefore being quenched by the addition of saturated NH4Cl solution (10 ml)
6. extractionThe aqueous layer was extracted with EtOAc (3×10 ml)
7. washthe combined organic phases were washed with brine (15 ml)
8. dry with materialbefore being dried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customto give the crude product
12. customThis was purified by column chromatography on silica
13. washeluting with petrol/EtOAc (100:5)

ORD record

ord-b32e6de2f21a466fb2235fdb00c33b94

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242954B2