tert-Butyldimethylsilyl chloride → HCID 18386565, compound

Temperature

0 °C

To a stirred, cooled (0° C.) solution of 188 mL (658 mmol) of a 3.5 M solution of cyclopropylacetylene in toluene was added 200 mL of THF. The solution was re-cooled to 0° C. and treated with 264 mL (660 mmol) of a 2.5 M solution of n-BuLi in hexanes over 15 min. The solution was stirred an additional 10 min. at 0° C. and treated with 100 g(663 mmol) of t-butyldimethylsilyl chloride in 60 mL of THF over 10 min. After stirring 90 min. at 0° C. the reaction was quenched with saturated aq. NH4Cl and poured into 500 mL of water. The mixture was extracted with 500 mL of ether, and the organic extract was washed three times with water and once with brine. Concentration under reduced pressure followed by distillation afforded 49 g(42%) of 1-(t-butyldimethylsilyl)-2-cyclopropylacetylene as a colorless oil (b.p. 39-42° C. at 0.5 torr). 1H NMR (CDCl3, 300 MHz) δ 1.17-1.24(m, 1H); 0.95(s, 9H); 0.61-0.75(m, 4H); 0.00(s, 6H).

1. stirringAfter stirring 90 min. at 0° C. the reaction
2. customwas quenched with saturated aq. NH4Cl
3. additionpoured into 500 mL of water
4. extractionThe mixture was extracted with 500 mL of ether
5. extractionthe organic extract
6. washwas washed three times with water
7. concentrationConcentration under reduced pressure
8. distillationfollowed by distillation

ORD record

ord-11be4afb6182496fb40256fcab76b998

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06303780B1