Some common heterocyclic compound, 326-58-9, name is Benzo[d][1,3]dioxol-5-yl acetate, molecular formula is C9H8O4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. COA of Formula: C9H8O4
General procedure: (i) [Ir(coe)2Cl]2 (0.9 mg, 0.1mol %) and aryl acetates 1 (1 mmol) were added to a flame-dried, nitrogen-purged septum-capped vial. The mixture was dissolved with THF (0.3 mL, 3.3 M), and diethylsilane (0.26 mL, 2 mmol) was added to the mixture. The septum on the vial was replaced by a screw cap with a Teflon liner under a N2 atmosphere [note: diethylsilane (bp 56 C and density 0.686 g/mL) is volatile]. The reaction mixture was stirred for 3-12 h at 60 C. Volatiles were removed in vacuo to afford silyl acetals, which were directly used for subsequent reactions without further purification. (ii) [Rh(nbd)Cl]2 (1.8 mg, 0.4 mol %), tris(4-methoxyphenyl)phosphine (8.4 mg, 2.4 mol %), norbornene (188 mg, 2 mmol), and THF (1 mL, 1M) were added to the crude silyl acetals (1 mmol). The septum on the vial was replaced by a screw cap with a Teflon liner, and the mixture was stirred at 120 C for 15 min. The reaction progress was monitored by GC/MS spectrometry. The resulting benzodioxasilines 3 were directly used for a subsequent reaction without further purification. For hindered substrates 3o-r, the resulting benzodioxasilines 3 were purified for the subsequent reactions; volatiles were removed in vacuo, and the resulting mixture was dissolved with pentane, filtered through a pad of Celite, and concentrated in vacuo. The crude product was purified by MPLC (hexanes/EtOAc=80:1, 5mL/min, retention time 5-15 min). (iii) The crude benzodioxasilines 3 (1 mmol, THF, 1M) were diluted with diethyl ether (3 mL, 0.33 M) and cooled to -78 C. MeLi (3 mmol, 1.6 M in Et2O) were added into the reaction mixture at -78 C and stirred for 1 min. (iv) Trifluoromethanesulfonyl anhydride (1.2 mmol, 0.2 mL) was added into the reaction mixture. The reaction mixture was warmed to rt and stirred for 30 min. The reaction mixture was cooled to 0 C and saturated aqueous ammonium chloride solution was added. The mixture was extracted with diethyl ether three times. The combined organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. Volatiles were removed in vacuo, and the crude mixture was purified by MPLC to afford arylsilyl triflates 5 (hexanes/EtOAc=40:1, 5mL/min, retention time 6-20 min).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 326-58-9, its application will become more common.
Reference:
Article; Asgari, Parham; Dakarapu, Udaya Sree; Nguyen, Hiep H.; Jeon, Junha; Tetrahedron; vol. 73; 29; (2017); p. 4052 – 4061;,
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