Ammonium Chloride → HCID 131723398, compound

Participants

Reaction Steps

To a solution of 2-iodo-3-quinoline carboxaldehyde (3 g, 10.6 mmol) in THF (25 ml) at −5° C., vinylmagnesium bromide (1 M solution, 10.8 ml, 10.8 mmol) was added. It was stirred at that temperature until the starting material disappears, which takes about one hour. N-butyllithium (8.5 ml, 2.5 M soln, 21.2 mmol) was added and the solution was stirred for another 25 min and then quenched with t-butanol (1.63 g, 22 mmol, only the C-2 anion is being quenched). Then a solution of di-tert-butyl dicarbonate (2.54 g, 11.6 mmol) was added and the solution was stirred for 2 h at −5° C. The reaction was then worked up with MTBE (60 ml) and 10% ammonium chloride solution (25 ml). The organic layer washed again with saturated NaCl solution and it was concentrated to an orange oil which crystallised on standing at 0° C. overnight. It was used as such for alkylation experiments. Yield=2.8 g (92.7%)

Provenance & Evidence