Compound 2-Na

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Compound data: CIF

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

In a 20 mL scintillation vial, a stirring Et₂O solution (~10 mL) of 1 (100 mg, 0.102 mmol) was treated with a single equivalent of NaHDIPP (20 mg, 0.102 mmol). After 5 minutes of stirring, the solution was slowly treated with a single equivalent of NaCH₂Si(CH₃)₃ (10mg, 0.102 mmol), followed by stirring for 30 minutes. Volatiles were removed in vacuo to isolate 2-Na (103 mg, 0.098 mmol, 97%). Crystals of 2-Na were grown by slow evaporation of a concentrated Et₂ O solution of 2-Na at -34 °C. ¹H NMR (300 MHz, C₆D₆, 25 ºC, TMS) δ = 1.51 (d, ³J(H,H) = 6Hz, 36H, iPrCH₃), 4.74 (sept, ³J(H,H) = 6 Hz, 6H, iPrCH), 5.19 (t, ³J(H,H) = 6 Hz, 3H, p-ArH), , 7.82 (d, ³J(H,H) = 6 Hz, 6H, m-ArH); ¹³C NMR (300 MHz, C₆D_6, 25 ºC, TMS) δ = 26.03 (iPrCH), 26.03 (iPrCH₃), 117.24 (m-CH), 122.87 (p-CH), 153.79 (i-C), 160.31 (o-C); IR (KBr plate): = 3043 (w), 2955 (vs), 2865 (s), 1573(w), 1459 (s), 1400 (s), 1356 (w), 1314 (s), 1238 (vs), 1206 (s), 1107 (w), 886 (w), 745 (s); analysis (calcd., found for C₆₄H₁₀₀N₄Na₂O₄U): C (59.78, 59.73), H (8.03, 7.94), N (4.65, 4.88).

Alternative preparation of 2-Na. In a 20 mL scintillation vial, an Et₂O solution of 1 (100 mg, 0.102 mmol) was treated with a single equivalent of NH₂DIPP (18 mg, 0.102 mmol) and let stir for 5 minutes. The solution was then treated with two equivalents of NaCH₂TMS (20 mg, 0.102 mmol), slowly, and the solution was left to stir for an additional 30 min. Excess solvent was removed in vacuo and analysis of the crude material by ¹H NMR spectroscopy revealed formation of 2-Na in good yield.