Reacción #1144077

Ecuación de reacción

5-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one

SOCl2

→

5-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-one

Disolventes

Et2O

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONThe reaction mixture was poured onto ice-water and more Et20
2. 2
   workup.ADDITIONwas added
3. 3
   OtroThen the Et20 phase was collected
4. 4
   Extracciónwater phase was extracted by Et20 twice
5. 5
   Lavadothe combined Et20 layer was washed with brine
6. 6
   Otrodried over Na2S04
7. 7
   Concentraciónconcentrated
8. 8
   OtroThe residue was purified by silica gel chromatography

Procedimiento

To a suspension of 5-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one (18.5 g, 80 mmol) in Et2O (130 mL) was added SOCl2 (18 mL, 1 10 mmol) at r.t. and the mixture was stirred for 1 h. The reaction mixture was poured onto ice-water and more Et20 was added. Then the Et20 phase was collected and water phase was extracted by Et20 twice, the combined Et20 layer was washed with brine, dried over Na2S04, and concentrated. The residue was purified by silica gel chromatography to give 5-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-one 1HNMR (DMSO, 400 MHZ) δ 8.27 (s, 1H), 7.32-7.41 (m, 5H)S 6.55 (s, 1H), 4.92 (s, 2H), 4.65 (s, 2H). MS (M+H)+250.1/252.1.

Fuente