Acetyl chloride → Ethyl {4-[2-(allyloxy)-4-methylphenyl]-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl}(oxo)acetate hydrochloride salt

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (2-allyloxy-4-methyl-phenyl)-(2-amino-4,5,6,7-tetrahydro-benzo[b]thiophen-3-yl)-methanone (882 mg, 2.69 mmols) in ethanol (30 mL) was added ethyl 2,4-dioxopentanoate (426 mg, 378 μL, 1 eq) followed by acetyl chloride (846 mg, 766 μL, 4 eq), and the reaction was heated to 50° C. for 1 hour. The reaction was then concentrated in vacuo to give [4-(2-allyloxy-4-methyl-phenyl)-2-methyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-b]pyridin-3-yl]-oxo-acetic acid ethyl ester hydrochloride as a pale yellow oil 1 g (86% yield). LCMS (2 min acidic) 1.70 min 54-100% pure by UV, ES+/AP+ 450. HNMR (CDCl3)>90% pure 6.95 (d, J=7.0 Hz, 1H) 6.87 (d, J=7.0 Hz, 1H) 6.76 (s, 1H) 5.82 (m, 1H) 5.09-5.20 (m, 2H) 4.39-4.51 (m, 2H) 3.84-3.94 (m, 2H) 2.95 (s, 3H) 2.87-2.93 (m, 2H) 2.43 (s, 3H) 1.92-2.08 (m, 2H) 1.78-1.89 (m, 2H) 1.55-1.70 (m, 2H) 1.12 (t, J=7.1 Hz, 3H).

Provenance & Evidence