Acetic Acid → Ethyl 3-(4-methyl-1,3-thiazol-2-yl)-3-oxopropanoate

Temperatur

80 °C

NaH (60% in oil, 1.34 g, 33.5 mmol) was washed with isohexane (2×14 mL), suspended in toluene (25 mL), treated with diethyl carbonate (4.7 mL, 4.6 g, 38.8 mmol), heated to 80° C., treated dropwise over 20 min with a solution of 2-acetyl-4-methylthiazole (2.72 g, 19.2 mmol) in toluene (5 mL) and stirred at 80° C. for 2 h. The mixture was cooled to 0° C., treated dropwise with HOAc (4.65 mL, 4.9 g, 81 mmol) followed by ice (25 g) and water (50 mL) and stirred for 30 min. The aqueous phase was extracted with toluene (50 mL), the combined organic phase was washed with water (50 mL), dried (MgSO4) and concentrated in vacuo to give the crude product (3 g, 74%) as a dark red oil, used in the next step without further purification; NMR δH (400 MHz, CDCl3) 1.26 (3H, t, J 7.2 Hz), 2.92 (3H, s), 4.14 (2H, s), 4.18-4.25 (2H, m) and 7.31 (1H, s).

1. temperatureThe mixture was cooled to 0° C.
2. stirringstirred for 30 min
3. extractionThe aqueous phase was extracted with toluene (50 mL)
4. washthe combined organic phase was washed with water (50 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo

ORD-Eintrag

ord-f39492cb4dc843edad1063bf49cffa23

Quelldatensatz

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07875600B2