有机合成英文文献翻译2.pdfVIP

Organic Syntheses, Vol. 81, p. 254-261 (2005); Coll. Vol. 11, p. 874-878 (2009). PREPARATION OF PIVALOYL HYDRAZIDE IN WATER (Propanoic acid, 2,2-dimethyl-, hydrazide) O O + NaOH/H O H NNH · H O 2 Cl 2 2 2 NHNH2 Submitted by Bryan Li,1 Raymond J. Bemish, David R. Bill, Steven Brenek, Richard A. Buzon, Charles K-F Chiu and Lisa Newell. Checked by Claire Coleman and Peter A. Wipf. 1. Procedure Pivaloyl hydrazide. A 1-L, three-necked, round-bottomed flask equipped with a Teflon-coated thermocouple and mechanical stirrer is charged with 400 mL of water and sodium hydroxide (12.87 g, 322 mmol), and the resulting mixture is stirred until all of the solids dissolve (Note 1). Hydrazine (35% aqueous solution, 36.83 g, 400 mmol) is then added in one portion. The mixture is cooled in an ice-water/acetone bath to an internal temperature of –5 to 0 °C, and trimethylacetyl chloride (38.6 mL, 320 mmol) is added dropwise (Note 2) over a period of 40-60 min while maintaining the reaction temperature between –5 and 0 °C (Note 3). The reaction mixture is then transferred to a 1-L, pear-shaped flask and concentrated to a volume of ca. 100 mL by rotary evaporation (at ca. 100 mm) (Notes 4, 5) and the resulting suspension is filtered (Note 6). The filtrate is further concentrated to a volume of ca. 40 mL (Note 7) and 100 mL of toluene is then added. The resulting solution is transferred to a three- necked, round-bottomed flask equip