methyl 2-hex-1-ynylbenzoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Treatment of methyl 2-(1-hexyn-1-yl)benzoate (157) (2.29 g, 10.6 mmol) with a mixture of N,O-dimethylhydroxylamine hydrochloride and nBuLi gave 2.0 g (77%) of the title compound (158) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 0.92 (t, J=7.2 Hz, 3H), 1.40-1.60 (m, 4H), 2.39 (t, J=7.0 Hz, 2H), 3.32 (br s, 3H), 3.50 (br s, 3H), 7.26-7.35 (m, 3H), 7.37-7.45 (m, 1H). LCMS (APCI): m/z 246 (M+H)+.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Coupling of 2-iodobenzoate (3.0 g, 11.5 mmol) with 1-hexyne (2.71 mL, 22.9 mmol) using Pd(PPh3)2Cl2 and CuI in DMF at room temperature gave 2.23 g (90%) of compound 157 as a brown oil. 1H NMR (400 MHz, CDCl3): δ 0.95 (t, J=7.3 Hz, 3H), 1.45-1.55 (m, 2H), 1.55-1.65 (m, 2H), 2.47 (t, J=7.0 Hz, 2H), 3.91 (s, 3H), 7.26-7.33 (m, 1H), 7.37-7.44 (m, 1H), 7.50 (d, J=7.7 Hz, 1H), 7.87 (d, J=7.9 Hz, 1H). LCMS (APCI): m/z 217 (M+H)+. at room temperature