2-(2-METHOXY-PHENYL)-THIAZOLE-4-CARBALDEHYDE synthesis

10synthesis methods

Product Name:2-(2-METHOXY-PHENYL)-THIAZOLE-4-CARBALDEHYDE
CAS Number:885279-11-8
Molecular formula:C11H9NO2S
Molecular Weight:219.26

[2-(2-METHOXY-PHENYL)-THIAZOL-4-YL]-METHANOL

187793-07-3
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2-(2-METHOXY-PHENYL)-THIAZOLE-4-CARBALDEHYDE

885279-11-8
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$246.00/250mg

Yield:885279-11-8 81 %

Reaction Conditions:

with pyridinium chlorochromate in dichloromethane at 20;

Steps:

3.1.7. Preparation of 2-(2-Methoxyphenyl)thiazole-4-carbaldehyde (5)

Under stirring at room temperature, PCC (1.46 g, 6.8 mmol) was dissolved in 45 mL of dichloromethane, and a solution of compound4(1.00 g, 4.5 mmol) in dichloromethane (40 mL) was added dropwise to it. After 4 h of reaction, the mixture was washed with 10% hydrochloric acid (30 mL × 2) and extracted with ethyl acetate (50 mL × 3). The organic layer was washed with brine (50 mL), water (50 mL × 2), then dried over anhydrous Na₂SO₄, filtered by suction, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel using petroleum ether and ethyl acetate (4:1,v/v) as eluent to obtain the target compound5as a white solid with 81% yield, mp. 81-83 °C;¹H NMR (400 MHz, CDCl₃) δ 10.14 (s, 1H), 8.49 (dd,J= 7.9, 1.7 Hz, 1H), 8.22 (s, 1H), 7.63-7.44 (m, 1H), 7.11 (ddd,J= 22.3, 14.6, 4.7 Hz, 2H), 4.06 (s, 3H).¹³C NMR (100 MHz, CDCl₃) δ 185.4, 163.7, 156.6, 153.7, 131.7, 128.8, 128.0, 121.3, 111.4, 55.6.

References:

Gao, Yongyue;He, Xingxing;Yan, Lili;Zhang, Hongyu;Liu, Sijia;Ma, Qian;Zhang, Peiyao;Zhang, Yan;Zhang, Zijun;Wang, Ziwen;Lu, Aidang;Wang, Qingmin [Molecules,2023,vol. 28,# 7,art. no. 3032]