Reacción #658245

Ecuación de reacción

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

SOCl2

→

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

Disolventes

Et2O

Et2O

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   OtroThen the Et2O phase was collected
3. 3
   Extracciónwater phase was extracted by Et2O twice
4. 4
   Lavadothe combined Et2O layer was washed with brine
5. 5
   Secadodried over Na2SO4
6. 6
   Concentraciónconcentrated
7. 7
   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, 110 mmol) at r.t. and the mixture was stirred for 1 h. The reaction mixture was poured onto ice-water and more Et2O was added. Then the Et2O phase was collected and water phase was extracted by Et2O twice, the combined Et2O layer was washed with brine, dried over Na2SO4, 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), 6.55 (s, 1H), 4.92 (s, 2H), 4.65 (s, 2H). MS (M+H)+ 250.1/252.1.

Fuente