Hydrochloric Acid → (3s)-3-(Tert-butyldimethylsiloxy)-5-phenyl-1-pentyne

Temperature

0 °C

Following a procedure of Noyori (Suzuki, M. et al., J. Med. Chem. 41, 3084-3090 (1998)); Imidazole (919.1 mg, 13.5 mmol, 1.8 eq.) and t-butylchlorodimethylsilane (1.35 g, 9.0 mmol) were added to a solution of (S)-5-phenylpent-1-yn-3-ol 86 (1.2 g, 7.5 mmol, 1 eq.) in CH2Cl2 (18 ml), cooled to 0° C. The reaction mixture was then stirred at room temperature for 14 h before being poured into 1 M HCl (50 ml). The mixture was extracted with 40/60 petroleum ether (3×50 ml). The combined organic phases were washed with brine (50 ml) before being dried (MgSO4), filtered and concentrated to give the crude product. This was purified by column chromatography on silica, eluting with petrol/Et2O (99:1), giving the title product 88 as a clear, colourless oil (1.77 g, 86%). Analytical data consistent with the literature (Kiyotsuka, Y. et al., Org. Lett. 10, 1719-1722 (2008); Sato, F. et al., EP 1211241 A1, Taisho Pharmaceutical co., LTD (2002)).

1. extractionThe mixture was extracted with 40/60 petroleum ether (3×50 ml)
2. washThe combined organic phases were washed with brine (50 ml)
3. dry with materialbefore being dried (MgSO4)
4. filtrationfiltered
5. concentrationconcentrated
6. customto give the crude product
7. customThis was purified by column chromatography on silica
8. washeluting with petrol/Et2O (99:1)

ORD record

ord-7a5b4608b20442688372341863920dc2

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242954B2