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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 518555Erstellt: 25. Oktober 2026

Potassium Carbonate → 2-Methyl-5-methylsulfonyl-2,3-dihydro-1-benzofuran

https://huagongshe.com/reaction/518555

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktPotassium CarbonateHCID 11430—
EduktL-ProlineHCID 145742—
Edukt5-Bromo-2-methyl-2,3-dihydro-1-benzofuranHCID 13301601—
EduktHCID 178504973HCID 178504973—
KatalysatorCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
LösungsmittelDimethyl SulfoxideHCID 679—
Produkt2-Methyl-5-methylsulfonyl-2,3-dihydro-1-benzofuranHCID 11802201950%

Reaktionsschritte

A mixture of 5-bromo-2-methyl-2,3-dihydro-1-benzofuran (1.0 g, 4.72 mmol), CH3SO2Na (730 mg, 7.08 mmol), L-proline (110 mg, 0.94 mmol), K2CO3 (120 mg, 0.94 mmol) and CuI (89 mg, 0.47 mmol) in DMSO (10 mL) was irradiated at 140° C. for 2 h under microwave. The mixture was extracted with EtOAc (2×30 mL). The combined organic layers were washed with brine (30 mL), dried over Na2SO4, filtered and concentrated to give the crude product that was purified by column chromatography on silica gel (PE/EA=2/1) to give the title compound (500 mg, 50%). 1H NMR (CDCl3, 400 MHz) δ 7.71-7.70 (m, 2H), 6.86-6.82 (m, 1H), 5.08-5.03 (m, 1H), 3.41-3.35 (m, 1H), 3.02 (s, 3H), 2.89-2.83 (m, 1H), 1.56 (d, J=6.4 Hz, 3H).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09115114B2
Quelldatensatzuspto-grants-2015_08
ORD IDord-4011f321c8704046bfcacf4598e51d74
Quellennotizuspto-grants-2015_08