Water → N-methoxy-N-methyl-2-phenylbutanamide

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To a stirred solution of pyridine (33.1 mL, 40.9 mmol) and N,O-dimethylhydroxylamine hydrochloride (26.0 g, 26.7 mmol) in anhydrous CH2Cl2 (300 mL) at 0° C. was added dropwise 2-phenylbutyryl chloride (37.4 g, 20.5 mmol) dissolved in THF (100 mL). The reaction mixture was stirred overnight at RT. H2O (300 mL) was added, and the mixture was extracted with CH2Cl2 (2×200 mL). The combined extracts were washed successively with 5% aqueous HCl (300 mL), 5% aqueous NaHCO3 (300 mL), H2O (300 mL), and brine (300 mL). The mixture was dried over Na2SO4, filtered, and concentrated to afford 41.6 g (98%) of 14 as a colorless oil which was used without further purification. 1HNMR (400 MHz, CDCl3): δ 0.87 (t, J=7.3 Hz, 3H), 1.74 (h, J=7.1 Hz, 1H), 2.08 (h, J=7.1 Hz, 1H), 3.14 (s, 3H), 3.46 (s, 3H), 3.88 (br s, 1H), 7.19-7.33 (m, 5H).

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