Ethyl 2-(hydroxyMethyl)thiazole-4-carboxylate synthesis

5synthesis methods

Product Name:Ethyl 2-(hydroxyMethyl)thiazole-4-carboxylate
CAS Number:40235-65-2
Molecular formula:C7H9NO3S
Molecular Weight:187.22

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Ethyl 2-(hydroxyMethyl)thiazole-4-carboxylate

40235-65-2
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Yield:40235-65-2 100%

Reaction Conditions:

with sodium tetrahydroborate in tetrahydrofuran at 0 - 25; for 2 h;

Steps:

Ethyl 2-(hydroxymethyl)thiazole-4-carboxylate (10).

A solution of compound 9 (2.27 g, 12.26 mmol) in dry THF (25.00 mL) was cooled to 0 °C and NaBH₄ (0.23 g, 6.13 mmol) was added portionwise. The reaction was stirred at 25 °C for 2 h. A saturated solution of NH₄Cl was added and the aqueous phase was extracted with DCM (3 x 20.00 mL). The combined organic layers were dried over Na₂SO₄, filtered and evaporated. Title compound was obtained without any further purification (quantitative yield). ESI-MS m/z 188 [M+H]⁺;¹H NMR (300 MHz, CDCl₃) δ 8.11 (s, 1H), 4.98 (s, 2H), 4.38 (q, J = 7.1 Hz, 2H), 3.36 (br s, 1H), 1.37 (t, J =7.1 Hz, 3H).

References:

Brindisi, Margherita;Maramai, Samuele;Grillo, Alessandro;Brogi, Simone;Butini, Stefania;Novellino, Ettore;Campiani, Giuseppe;Gemma, Sandra [Tetrahedron Letters,2016,vol. 57,# 8,p. 920 - 923] Location in patent:supporting information