((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 NH4Cl 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 eluting 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 NH4Cl 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
12. washeluting with 5-7% EtOAc in hexanes

ORD record

ord-6e7d8a58f64447d79013c6c200fe861f

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08466148B2