Samarium(II) iodide (THF solution, typically 6 equivalents) is added to acid (pure), followed by the addition of amine (typically 18 or 36 equivalents) and water (typically 18 or 36 equivalents) under an inert atmosphere, and the mixture is vigorously stirred at room temperature. After a specified time (typically 2–5 h), excess SmI2 is oxidized by bubbling air through the reaction mixture. The reaction mixture is diluted with CH2Cl2 (30 mL) and HCl (1 N, 30 mL). The aqueous layer is extracted with CH2Cl2 (3 x 30 mL), the organic layer is bound, dried over Na2SO4, filtered, and concentrated. The crude product is purified by short-stoppered silica gel flash chromatography. Unless otherwise stated, all yields refer to individual yields.
Nonane-1,9-diol (Table 2, entry 7) was reacted according to general procedure method A with nonanoic acid (0.10 mmol), samarium(II) iodide (1.2 mmol), water (7.2 mmol), and triethylamine (7.2 mmol) at rt for 18 h. The reaction was followed by chromatography (1/10–1/1 ethyl acetate/hexane) to give the target compound 1,9-nonanediol in 88% yield.
