Reacción #1496012

Ecuación de reacción

6-bromo-2′,4′,5′,6′-tetrahydrospiro[chroman-2,3′-pyran]-4-one

phenylacetylene

→

6-(phenylethynyl)-2′,4′,5′,6′-tetrahydrospiro[chroman-2,3′-pyran]-4-one

Rendimiento 90.5%

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAn oven dried 3-necked round bottom flask
2. 2
   Otroequipped with condenser
3. 3
   OtroThe system was degas once again
4. 4
   OtroThe reaction was evaporated after 12 h
5. 5
   Otrothe residue was purified by flash chromatography (12 g silica gel
6. 6
   Lavadoeluted with EA in hexane in a gradient of 0-25%, v/v)

Procedimiento

An oven dried 3-necked round bottom flask equipped with condenser was charged with 6-bromo-2′,4′,5′,6′-tetrahydrospiro[chroman-2,3′-pyran]-4-one (223 mg, 0.75 mmol), TEA (3 mL) and DEA (0.8 mL) under N2 atmosphere. To this solution was added CuI (5.7 mg, 0.03 mmol), PdCl2(PPh3)2 (21 mg, 0.03 mmol) and PPh3 (16 mg, 0.06 mmol). The system was degas once again, then phenylacetylene (0.41 mL, 3.75 mmol) was added and the mixture was heated to 80° C. (oil bath) with stirring. The reaction was evaporated after 12 h and the residue was purified by flash chromatography (12 g silica gel, eluted with EA in hexane in a gradient of 0-25%, v/v) to afford 6-(phenylethynyl)-2′,4′,5′,6′-tetrahydrospiro[chroman-2,3′-pyran]-4-one (216 mg, yield: 90%). MS ESI+ve m/z 319 (M+H)+.

Fuente