Diethyl Ether → HCID 10013562, compound

Participants

Reaction Conditions

Reaction Steps

In Step III of FIG. 1, a suspension of 1.00 g (2.78 mmoles) of bis(4-trimethylsilylethynylphenyl)methane [Compound (4)] in 50 ml anhydrous deaerated methanol was treated with enough anhydrous ethyl ether to dissolve all solid particles at 25° C. Anhydrous potassium carbonate (300 mg) was added and the mixture was stirred at 25° C. under argon for 16 hours. The solvent was removed and the solid residue was dissolved in 50 ml dichloromethane, treated with 5 g of silica gel and evaporated to dryness. The powder was placed on top of a 40 cm (I.D. 30 mm) column of silica gel (EM Labs, 70-230 mesh) and the column was developed with passage of hexane. A crystalline white solid [Compound (6)] was recovered from the eluate: 0.60 gm (2.78 mmoles, 100%); mp 63°-64° C. After drying at 56° C./0.01 mm Hg inside an Abderhalden apparatus for 2 hours, the mp increased to 65.5°-66.5° C. IR(KBr) 3280 (very strong, sharp, --C≡C--H), 2100 (weak, sharp, --C≡C--) and 1500 cm-1 (medium, sharp, C=C); MS (70 eV) m/e 216 (molecular ion); NMR(CDCl3) δ 3.03 (s, 2H, C≡C--H), 3.95(s, 2H, CH2), 7.10 and 7.43 ppm (q, 8H, JAB =8.0 Hz, aromatic).

Provenance & Evidence