Methyl iodide → HCID 18443280, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of trimethylethylenediamine (0.45 mL, 3.48 mmol) in THF (9 mL) at −20° C. was added Butyllithium 1.6M in hexanes (2.11 mL, 3.8 mmol). The solution was stirred at −20° C. for 15 min. A solution of 4-Triisopropylsilanyloxy-benzaldehyde (0.922 g, 3.31 mmol) was added dropwise and the solution stirred for 15 min at −20° C. Bu 16M in hexanes (6.21 ml, 9.93 mmol) was added dropwise and the solution kept in the freezer at −20° C. for 26 hours. The solution was cooled to 40° C. and methyl iodide (3.71 mL, 59.60 mmol) was added. The solution was allowed to reach room temperature and further stirred 30 ml. The reaction was quenched with saturated ammonium chloride (20 mL) and extracted with ethyl acetate (3×30 mL). The combined extracts were dried (MgSO4), concentrated under vacuum and purified by column chromatography (silica gel, hexanes/Ethyl acetate 20:1, Rf0.085) (49%). 1H-NMR (CDCl3, 200.15 MHz): δ 10.1 (s, 1H), 7.69 (d, 1H, J=8.3), 6.80 (dd, 1H,J=8.6, 2.4), 6.72 (s, 1H), 0.61 (s, 3H), 1.33–1.19 (m, 3H), 1.12 (s,18H).

Provenance & Evidence