((1,1-Dimethyl-2-propynyl)oxy)trimethylsilane → HCID 59354751, compound

Temperature

-78 °C

To a −78° C. stirred solution of trimethyl (2-methylbut-3-yn-2-yloxy) silane (11.79 g, 75.15 mmol) in dry THF (100 mL), n-BuLi (14.08 mL, 22.54 mmol, 1.6 M in hexane) was added dropwise over 10 minutes under an inert atmosphere. After being stirred for 30 min at −78° C., a solution of 4-chloro-N-methoxy-N-methylbenzamide (5.0 g, 25.0 mmol) in dry THF (10 mL) was added to reaction mixture and stirring was continued for an additional 1 h at −78° C. The reaction mixture was quenched with a saturated NH4C solution and extracted with EtOAc (2×100 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried over Na2SO4, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography elating with 5-7% EtOAc in hexanes to afford 1-(4-chlorophenyl)-4-methyl-4-(trimethylsilyloxy)pent-2-yn-1-one (3.8 g, 57%) as a light green oil.

1. additionwas added dropwise over 10 minutes under an inert atmosphere
2. stirringstirring
3. waitwas continued for an additional 1 h at −78° C
4. customThe reaction mixture was quenched with a saturated NH4C solution
5. extractionextracted with EtOAc (2×100 mL)
6. washThe combined organic layers were washed with water (50 mL) and brine (50 mL)
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto obtain the crude product
11. customThe crude material was purified via silica gel column chromatography

ORD record

ord-85b3ef67bd1f435da1840ebbf893f151

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08933074B2