2-Methyl-3-butyn-2-ol → HCID 69322534, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of product from Example 13 (33 mg, 0.08 mmol), 2-methylbut-3-yn-2-ol (10 mg, 0.1 mmol), CuI (2 mg, 0.01 mmol and Pd(Ph3P)4 (30 mg, 0.03 mmol) in triethylamine (10 mL) was heated at 100° C. for 1 hour. The mixture was then cooled to room temperature and concentrated under reduced pressure. The residue was purified by chromatography (hexane-EtOAc 1:1) to afford 20 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 0.95 (t, J=7 Hz, 3H), 1.40 (sextet, J=7 Hz, 2H), 1.67 (quintet, J=7 Hz, 2H), 2.34 (s, 3H), 3.85 (s, 3H), 3.95 (t, J=7 Hz, 2H), 5.50 (s, 1H), 6.72 (s, 1H), 7.13 (d, J=9 Hz, 1H), 7.43 (dd, J=9 Hz, 3 Hz, 1H), 7.66 (d, J=3 Hz, 1H); MS (ESI) m/z 420 (M+H)+. Anal calcd for C22H26ClNO3S: C, 62.92; H, 6.24; N, 3.34. Found: C, 62.85; H, 6.28; N, 2.92.

Provenance & Evidence