N-Formylmorpholine → 2-(2-Chloro-4-methoxyphenoxy)-1,3-thiazole-5-carbaldehyde

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of Example 30A (12 g, 49.9 mmol) in tetrahydrofuran (100 mL) was added butyllithium (2.5 M in hexanes, 21 mL, 52.5 mmol) drop wise over 10 minutes at −78° C. under nitrogen. The mixture was stirred at −78° C. for 1 hour, and was treated with 4-formylmorpholine (5.3 mL, 52.4 mmol) drop wise over 5 minutes. The reaction was allowed to warm to 25° C. and was stirred for 2 hours. The reaction was cooled to 0° C. and quenched with saturated NH4Cl (600 mL). The resulting mixture was extracted with ethyl acetate (2×200 mL) and the combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated to provide 13.2 g of the title compound (98%) as a light yellow liquid. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.83 (s, 3H) 7.06 (dd, J=9.19, 2.94 Hz, 1H) 7.28 (d, J=2.94 Hz, 1H) 7.57 (d, J=9.19 Hz, 1H) 8.28 (s, 1H) 9.88 (s, 1H); MS (ESI) m/z 269.9 (M+H)+.

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