Methanol → Triethylamine, 2',2''-dichloro-1,1-dimethyl-

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Reaction Conditions

Reaction Steps

Thionyl chloride (30 mL, 409.2 mmol) was diluted in chloroform (40 mL) and stirred at 20° C. 2,2′-(Tert-butylazanediyl)diethanol (30 g, 186 mmol) in chloroform (20 mL) was added dropwise over 45 minutes. The resulting mixture was stirred for 18 hours at 20° C. and refluxed for 2 hours. The mixture was cooled and methanol (˜10 mL) was added, followed by ethyl ether (˜50 mL). The resulting precipitate was filtered, washed with ethyl ether and dried under vacuum to give the title material (35 g, 81%) as the HCl salt. 1H NMR (400 MHz, CDCl3) δ ppm: 1.60 (9H, s), 3.20 (2H, s), 3.68 (2H, s), 4.12-4.19 (2H, m), 4.21-4.28 (2H, m), 12.66 (1H, s).

Provenance & Evidence