Phenylacetylene → HCID 22042608, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.18 g of phenylacetylene (1.75 mmol) in 5 mL of THF was added dropwise 0.76 mL of n-BuLi (2.5M in hexane) at −78° C. The color of the solution turned dark blue and the mixture was stirred at −78° C. for 30 min. Then 0.5 g of N-methyl-N-(4-trifluoroacetyl-phenyl)-benzenesulfonamide (Example 22, Step A) in 5 ml of THF was added and the resultant mixture stirred at −78° C. for 2 h. After this time the reaction was quenched by the addition of a saturated aqueous solution of ammonium chloride and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography on silica gel (hexanes:EtOAc, 7:3) to give the title compound. 1H NMR (CDCl3) δ 3.19 (s, 3 H), 3.26 (br s, 1 H), 7.17 (d, J=8.7 Hz, 2 H), 7.34-7.60 (m, 10 H), 7.74 (d, J=8.7 Hz, 2 H). Mass Spectrum (CI+) m/e=446.0 (M+1).

Provenance & Evidence