Acetonitrile → HCID 58109332, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence