With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.230642-84-9,4-Vinyl-2,3-dihydrobenzofuran,as a common compound, the synthetic route is as follows.
To a flame-dried 1L three necked round bottom flask equipped with a magnetic stirrer was added N,N,2-trimethyl propionamide (17.8mL, 0.138mol) and anhydrous methylene chloride (200mL). The mixture was stirred to give a solution under argon and cooled to -15C. Trifluoromethanesulfonic anhydride (26mL, 0.154mol) was added via syringe and the resulting mixture was stirred at -15C for 10 minutes. A solution of [] (from Part D)(17.5g, 0.12mol), and collidine (21mL, 0.155mol) in anhydrous methylene chloride (30mL) was added at -15C. After the addition was completed, the reaction mixture was heated to reflux and stirred for 20 hours. The solvent was removed on a rotary evaporator and the residue oil was washed with ether (3x100mL) The residue was then dissolved in methylene chloride (150mL). Water (150mL) was added and the mixture was refluxed for 6 hours. After cooling to room temperature, the phases were separated. The aqueous layer was extracted with methylene chloride (2¡Á100mL). The rich organic layers were combined, washed with brine (200mL) and dried over anhydrous sodium sulfate. After removal of sodium sulfate by filtration, the filtrate was concentrated to give an oil which was purified by silica gel chromatography using 5-10% EtOAc/hexane as the eluent to give 19.0g (73%) title compound as a white crystalline compound. HPLC, 100A% at 220nm. 1H NMR (CDCl3) d, 7.14 (t, J=7.8Hz, 1H), 6.72 (t, J=8.2Hz, 2H), 4.52-4.65 (m, 2H), 3.50 (dd, J=7.0, 16.4Hz, 1H), 3.08-3.41 (m, 4H), 1.38 (s, 3H), 0.83 (s, 3H).
230642-84-9, The synthetic route of 230642-84-9 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; EP1041980; (2005); B1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem