New learning discoveries about 5381-20-4

5381-20-4 Thianaphthene-3-carboxaldehyde 227328, abenzothiophene compound, is more and more widely used in various.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5381-20-4,Thianaphthene-3-carboxaldehyde,as a common compound, the synthetic route is as follows.

3-(Benzo[d]thiophen-3-yl)acrylic Acid Methyl Ester To a stirred suspension of lithium chloride (1.02 g; 24.1 mmol) in dry MeCN (180 mL) under nitrogen at room temperature was added drop-wise at 15 min intervals trimethyl phophonoacetate (4.39 g; 24.0 mmol) in dry MeCN (15 mL), DBU (3.05 g; 20.0 mmol) in dry MeCN and finally benzo[d]thiophen-3-carboxaldehyde (3.24 g; 20.0 mmol) in dry MeCN (30 mL). The reaction was allowed to stir at room temperature until completion, as determined by TLC. The reaction mixture was filtered and concentrated under reduced pressure. The resulting yellow oil was dissolved in DCM (60 mL) and washed with distilled water (3*20 mL) and saturated sodium chloride solution (3*20 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give a red oil. Purification by column chromatography on silica gel using DCM as the eluent followed by recrystallization with hexanes gave a pale yellow crystalline solid (2.63 g; 60%): mp 63-65 C.; Rf0.68 (D); Rf0.45 (F); numax (KBr): 1708, 1281, 1159, 972 cm-1; m/z (EI): 218.0, 187.0, 159.1, 88.8; deltaH (CDCl3, 200 MHz): 3.84 (3 H, s), 6.54 (1 H, d, J=15.8), 7.41 (1 H, td, J=5.6 and 1.8), 7.47 (1 H, td, J=5.6 and 1.6), 7.76 (1 H, s), 7.88 (1 H, dq, J=7.0 and 2.2), 7.98 (1 H, dd, J=16.4 and 0.6), 8.02 (1 H, dq, J=5.0 and 1.4); deltaC (CDCl3, 101 MHz): 52.1, 118.6, 122.4, 123.3, 124.6, 125.4, 128.4, 131.9, 136.9, 137.4, 140.8, 167.9; m/z calculated for C12H10O2S: 218.0402 (M+), found 218.0401 (M+).

5381-20-4 Thianaphthene-3-carboxaldehyde 227328, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; Queen’s University at Kingston; US2003/114441; (2003); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem