Acetic Anhydride → 1-(4,4-dimethyl-3,4-dihydroisoquinolin-2(1H)-yl)ethanone

Participants

Reaction Steps

A solution of acetic anhydride (1.17 ml, 12.4 mmol) was added dropwise to a stirred, ice-cooled solution of 4,4-dimethyl-1,2,3,4-tetrahydro-isoquinoline (1.0 g, 6.2 mmol) (for preparation see J. Org. Chem., 1983, 48, 5348) in dry dichloromethane (5 ml). The cooling bath was removed and the solution was stirred for 2 h at room temperature. The reaction mixture was then concentrated in vacuo to give the title compound (D2) as an oil (1.1 g, 87%), δH (CDCl3, rotamers observed)/ppm 1.28, 1.32 (6H, 2×s), 2.20, 2.22 (3H, 2×s), 3.43, 3.61 (2H, 2×s), 4.66, 4.77 (2H, 2×s), 7.07-7.37 (4H, m).

Provenance & Evidence