4H-1-Benzopyran-4-one, 7-[(methylsulfonyl)oxy]-2-phenyl- synthesis
- Product Name:4H-1-Benzopyran-4-one, 7-[(methylsulfonyl)oxy]-2-phenyl-
- CAS Number:796-60-1
- Molecular formula:C16H12O5S
- Molecular Weight:316.3285
Yield:796-60-1 67%
Reaction Conditions:
with triethylamine in tetrahydrofuran at 20;Cooling with ice;
Steps:
Synthesis of 4-oxo-2-phenyl-4H-chromen-7-ylmethanesulfonate (3a-i)
To a solution of 2a-i (1 mmol) in dry tetrahydrofuran(5 mL) methanesulfonyl chloride (1.5 mmol) and triethylamine(2 mmol) was added dropwise in an ice bath andstirred at room temperature overnight. Then the volatileswere evaporated under vacuum. To this residue water wasadded and it was extracted with ethyl acetate. The organicphase was dried with sodium sulfate and the solvent wasevaporated under vacuum. The product was purified bypreparative TLC (hexane: EtOAc, 3:2). 4-oxo-2-phenyl-4H-chromen-7-yl methanesulfonate (3a) White crystal, yield:67%, mp:120-121 °C, IR (KBr, cm-1):1638, 1335 (S = O), 1199; 1H NMR (500MHz, DMSO-d6):δ 8.17 (d, J = 8.4 Hz, 1H, H5), 8.15 (d, J = 8.4 Hz, 2H, H2’,6’), 7.91 (d, J = 1.9 Hz, 1H, H8), 7.67-7.59 (m, 3H,H3’,4’,5’), 7.50 (dd, J = 8.4, 1.9 Hz, 1H, H6), 7.13 (s, 1H,H3), 3.55 (s, 3H, CH3SO2). Anal. calcd. for C16H12O5S: C,60.75; H, 3.82; O, 25.29. Found: C, 60.81; H, 4.02;O, 25.53.
References:
Javadi, Mahdiyeh H. S.;Iraji, Aida;Safavi, Maliheh;Montazeri, Hamed;Tarighi, Parastoo;Eftekhari, Samane;Navidpour, Latifeh;Mirfazli, Seyedeh Sara [Medicinal Chemistry Research,2021,vol. 30,# 9,p. 1677 - 1687]
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