2-(Trimethylsiloxy)-1,3-butadiene → HCID 68772490, compound

Participants

Reaction Conditions

Reaction Steps

2,4,5-Trifluoro-β-nitrostyrene (7.8 g, 38.4 mmol) and 2-trimethylsiloxy-1,3-butadiene (8.18 g, 57.6 mmol) were mixed in toluene (10 ml). The reaction was heated to 120° C. overnight. The reaction mixture was cooled to room temperature, concentrated and treated with trifluoroacetic acid (10 mL) and CH2Cl2 (10 mL) at 0° C. It was stirred for 30 minutes, then saturated NaHCO3 was added to adjust pH (˜7). The mixture was extracted with ethyl acetate (3×) and the combined organic extracts were washed with water and brine, and then concentrated. A minimum amount of methylene chloride was added to the residue to induce crystallization. The crystals were collected by filtration and the mother liquid was subjected to column chromatography (eluting with 25% ethyl acetate/hexane). The recrystallized and chromatographed material was combined to yield the title compound (7.0, 70%). 1H NMR (300 MHz, CDCl3) δ ppm 2.29-2.82 (m, 6H), 3.73-3.89 (m, 1H), 5.06-5.29 (m, 1H), 6.86-7.12 (m, 2H). MS (ESI) m/z 274 (M+H)+.

Provenance & Evidence