Acetonitrile → HCID 58109332, compound

Temperature

-78 °C

Dry THF (15 mL) was cooled to −78° C. and 2.5M n-BuLi (5.18 mL, 2.0 equiv.) was added. A solution of acetonitrile (680 μL, 2.0 equiv.) in dry THF (2 mL) was added dropwise over 2 min. The mixture was stirred at −78° C. for 1 h. A solution of 3-chloroacetophenone (835 μL, 6.468 mmol) in dry THF (2 mL) was added dropwise over 2 min. 30 min. The mixture was stirred at −78° C. for 30 min. and was warmed to rt slowly. After being stirred at rt for 15 min., the mixture was quenched with water (10 mL), diluted by ether (20 mL), washed with 2% aq HCl (15 mL). The aqueous layer was extracted with ether (2×10 mL). The combined organic layers were washed with satd aq NaHCO3 (5 mL) and brine (10 mL), and dried over Na2SO4. After filtration and concentration, the crude product (1.4 g, quant. yield) was used for next step without further purification. LC-MS Method 1 tR=1.40 min., m/z=219, 221 (M+Na).

1. custom30 min
2. stirringThe mixture was stirred at −78° C. for 30 min.
3. temperaturewas warmed to rt slowly
4. stirringAfter being stirred at rt for 15 min.
5. customthe mixture was quenched with water (10 mL)
6. additiondiluted by ether (20 mL)
7. washwashed with 2% aq HCl (15 mL)
8. extractionThe aqueous layer was extracted with ether (2×10 mL)
9. washThe combined organic layers were washed with satd aq NaHCO3 (5 mL) and brine (10 mL)
10. dry with materialdried over Na2SO4
11. filtrationAfter filtration and concentration

ORD record

ord-46c3fc4270324b7b83885cf7f80d2c77

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08575156B2