Chlorotrimethylsilane → HCID 12063077, compound

Participants

Reaction Conditions

Reaction Steps

1,4-Cyclohexadiene (0.47 mL, 5 mmol, 1 eq.) was dissolved in TBF (8 mL), cooled to −78° C. and s-BuLi (4.5 mL, 1.2 M, 5.5 mmol, 1.1 eq.) was added slowly. The resulting solution was treated with TMEDA (0.77 mL, 5 mmol, 1 eq.) and the reaction was allowed to warm to −45° C. over 2 hours. Me3SiCl (0.7 mL, 5.5 mmol, 1.1 eq.) was added, the reaction mixture was stirred for 1 hour at room temperature and then quenched with H2O and Et2O. The organic layer was separated and washed with H2O (2×30 mL), (aq) sat. NH4Cl (30 mL), brine (30 mL) and dried over MgSO4. Removal of the solvent in vacuo and distillation using Kugelrohr apparatus (30 mbar, 70° C.) afforded the product as colourless oil (0.53 g, 3.47 mmol, 70% yield): 1H NMR (400 MHz, CDCl3), δ 5.56 (2H, m, H-3), 5.55 (2H, m, H-4), 2.69 (2H, m, H-5), 2.22 (1H, m, H-2), 0.03 (9H, s, H-1); 13C NMR (100 MHz, CDCl3) δ 126.31 (C-3), 121.33 (C-4), 31.52 (C-5), 26.40 (C-2), −3.55 (C-1); IR (CDCl3, cm−1) 3027 (m, C—H), 2959 (m, C—H), 1622 (w, C═C), 743, (m, C—H); MS (FI+, m/z), 152.10 [M].

Provenance & Evidence