Water → HCID 59541078, compound

Participants

Reaction Steps

A solution of 2,2-Dimethyl-3-triisopropylsilanyloxy-propan-1-ol (1.39 g, 5.34 mmol) (Journal of the American Chemical Society, 123(39), 9687-9688; 2001) dissolved in ACN (14 ml), CCl4 (14 ml), and water (22 ml) was treated with sodium periodate (4.57 g, 21.4 mmol) and then RuCl3—H2O (33 mg, 0.16 mmol). After stirring at room temperature for approximately 2 hours, the reaction mixture was partitioned between DCM/water. The organic layers were collected, dried over MgSO4, filtered, and concentrated giving a black oil. Silica gel chromatography using 0-30% EtOAc in hexanes as eluant provided 1.23 mg (84%) of 2,2-dimethyl-3-triisopropylsilanyloxy-propionic acid. M−H=569.

Provenance & Evidence