Acetonitrile → HCID 57938623, compound

Participants

Reaction Steps

A mixture of 5 (300 mg, 0.732 mmol) available from procedure [0051] in triethyl amine (5 mL) and CH3CN (8 mL) was stirred with 3,3-dimethyl-1-butyne (12.3 mg, 0.15 mmol) and bis(triphenylphosphine)palladium (II) acetate (38.3 mg, 0.051 mmol) and heated to reflux under nitrogen. After 5 hours, the reaction mixture was cooled to rt and filtered. The filtrate was concentrated under vacuum and the residue was treated with H2O (10 mL), and extracted with CH2Cl2 (3×10 mL). The organic layers were combined and washed with brine and dried (Na2SO4). After removal of solvent under reduced pressure, the residue was purified via flash chromatography (silica gel, EtOAc/hexanes: 1/1) to furnish the t-butylacetylene 24(XLi340) as a yellow powder (271 mg, 90%): mp: 155-156° C.; IR (KBr) 2358, 1717, 1489, 1248, 1074, 803, 668 cm−1; 1HNMR (CDCl3) δ 1.25 (s, 9H), 1.45 (t, 3H, J=7.1 Hz), 4.05 (d, 1H, J=12.3), 4.45 (2H, J=7.1 Hz), 5.95 (d, 1H, J=12.3 Hz), 7.3-7.7 (m, 8H), 7.95 (s, 1H); MS (EI) m/e (relativity intensity) 412 (M+, 46), 365 (46), 337 (100), 322 (8), 277 (16), 219 (14). Anal. Calcd. For C26H25N3O2.½H2O, C 74.26, H 6.23, N 9.99. Found. C, 74.50; H, 6.29; N, 9.89.

Provenance & Evidence