Hydrochloric Acid → (S)-tert-Butyldimethyl(oct-1-yn-3-yloxy)silane

The procedure of Noyori (Suzuki, M., et al., J. Med. Chem. 41, 3084-3090 (1998)) was used. Imidazole (971 mg, 14.3 mmol) and t-butylchlorodimethylsilane (1.43 g, 9.51 mmol) were added to a solution of (S)-1-octyn-3-ol SI-8 (1.00 g, 1.16 ml, 7.92 mmol) in CH2Cl2 (18 ml), cooled to 0° C. The reaction mixture was then stirred at room temperature for 24 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 title compound SI-7 (1.89 g, 99%) as a clear, colourless oil. Analytical data consistent with the literature (Nicolaou, K. C. et al., A. J. Am. Chem. Soc. 107, 7515-7518 (1985); Cmrecki, V. et al., Tetrahedron 66, 6550-6564 (2010)).

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

ORD record

ord-ef0b8077dbd04974970447d63ba127c7

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242954B2