Reacción #340383

Ecuación de reacción

Triethylsilane

7-methoxy-isothiochroman-4-one-3-carboxylic acid methyl ester

→

7-methoxy-isothiochroman-3-carboxylic acid methyl ester

Rendimiento 70.6%

Disolventes

trifluoroacetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónwas concentrated under reduced pressure
2. 2
   workup.DISSOLUTIONThe resulting oil was dissolved in EtOAc (100 mL)
3. 3
   Lavadowashed with sat. NaHCO3 (3×75 mL)
4. 4
   Secadodried (MgSO4)
5. 5
   Concentraciónconcentrated
6. 6
   Otroto provide an oil
7. 7
   OtroThe oil was purified on silica using medium pressure chromatography (9:1 petroleum ether/EtOAc)

Procedimiento

Triethylsilane (8.08 mmol, 0.94 g) was added to a solution of 7-methoxy-isothiochroman-4-one-3-carboxylic acid methyl ester (0.51 g, 2.02 mmol) in trifluoroacetic acid (15 mL) at room temperature under N2. The reaction was allowed to stir at room temperature for 2 h and was concentrated under reduced pressure. The resulting oil was dissolved in EtOAc (100 mL) and washed with sat. NaHCO3 (3×75 mL). The organic extracts were combined, dried (MgSO4) and concentrated to provide an oil. The oil was purified on silica using medium pressure chromatography (9:1 petroleum ether/EtOAc) to provide 7-methoxy-isothiochroman-3-carboxylic acid methyl ester (0.34 g, 70%) as a pale yellow oil. 1H-NMR (300 MHz, CDCl3) δ 3.14 (m, 2H), 3.58-3.63 (d, J=15 Hz, 1H), 3.73-3.86 (m, 8H), 6.70 (d, J=3 Hz, 1H), 6.75 (dd, J=3, 9 Hz, 1H), 7.10 (d, J=9 Hz, 1H).

Fuente