tert-Butyl acetate → HCID 66869285, compound

Participants

Reaction Steps

Pd2(dba)3 (928 mg, 1.01 mmol) and (2′-dicyclohexylphosphanyl-biphenyl-2-yl)-dimethyl-amine (838 mg, 2.13 mmol) are added at RT under an atmosphere of argon to a solution of lithium hexamethyl disilazide in toluene (prepared by addition of n-BuLi (1.6 M in hexane, 24.3 ml, 38.85 mmol) to hexamethyl disilazane (6.27 g, 38.85 mmol) in toluene (100 ml) at −78° C.). The mixture is stirred at RT for 10 minutes, then it is cooled to −10° C. Acetic acid tert-butyl ester (4.12 g, 35.48 mmol) is added during 10 minutes. This mixture is canulated into a cold (−10° C.) solution of 1,3-dichloropyridine (5.00 g, 33.79 mmol) in toluene (40 ml). The mixture is warmed to RT and stirred for 2 h. TLC analysis indicated substantial conversion of starting material. Water was added, the resulting slurry is filtered, and the filtrate is extracted with EtOAc. The combined organic layers are dried over Na2SO4 and concentrated. Purification by FCC (hexane/EtOAc 100:0 to 92:8 to 85:15) yields the title compound. 1H NMR (CDCl3, 400 MHz): δ 1.39 (s, 9H), 3.47 (s, 2H), 7.58-7.60 (m, 1H), 8.31 (s,1H), 8.41-8.42 (m, 1H). ES+−MS: 228.3 [M+H]+.

Provenance & Evidence