N,N,N',N'-Tetramethylethylenediamine → HCID 10607879, compound

Participants

Reaction Conditions

Reaction Steps

1,4,-Cyclohexadiene (3.76 mL, 40 mmol, 1 eq.) was dissolved in THF (64 mL) and cooled to −78° C. s-BuLi (40 mL, 44 mmol, 1.1 eq.) was added dropwise and the resulting suspension was treated with TMEDA (6.12 mL, 40 mmol, 1 eq.). The reaction mixture was allowed to warm to −45° C. over 2 hours, TBDMSCl (6.6 g, 44 mmol, 1.1 eq.) in THF (20 mL) was added dropwise and the reaction stirred at room temperature for 1 hour. The reaction was quenched with Et2O and H2O and then extracted with Et2O (3×100 mL). The combined organic layers were washed with sat. NH4.Cl (aq.) (100 mL) and brine (100 mL), dried over MgSO4 and the solvent removed in vacuo. Distillation using Kugelrohr apparatus (125° C., 43 mbar) afforded the product as a colourless oil (5.9 g, 31 mmol, 77% yield). 1H NMR (CDCl3) δ 5.74 (2H, m, H-5), 5.55 (2H, m, H-6), 2.70 (2H, m, H-7), 2.41 (1H, m, H-4), 0.95 (9H, s, H-1), 0.01 (6H, s, H-3); C13 NMR (100 MHz, CDCl3) δ 134.5 (C-4), 121.2 (C-5), 29.3 (C-4), 27.2 (C-7), 26.2 (C-1), 17.7 (C-2), −6.2 (C-3); IR (neat, cm−1) 3029 (m, C—H), 2956 (m, C—H), 1667 (w, C═C); MS (CI, m/z) 195.16 [M+H+].

Provenance & Evidence