Reacción #67263

Ecuación de reacción

(7-bromo-2,3-dihydro-1,4-benzodioxin-2-yl)methanol

sodium methanesulfinate

L-proline

K2CO3

→

title compound

Rendimiento 182.2%

[7-(METHYLSULFONYL)-2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL]METHANOL

Rendimiento 182.2%

Disolventes

DMSO

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroflushed vial
2. 2
   workup.ADDITIONThe batches were mixed
3. 3
   workup.ADDITIONdiluted with water and HCl (1 N)
4. 4
   ExtracciónThe resulting solution was extracted with EtOAc
5. 5
   LavadoThe combined organic phases were washed with brine
6. 6
   Otrodried
7. 7
   Otropurified on flash column chromatography (isooctane/EtOAc/MeOH)

Procedimiento

4 batches of a mixture of (7-bromo-2,3-dihydro-1,4-benzodioxin-2-yl)methanol (0.5 g, 2.0 mmol), sodium methanesulfinate (85%) (0.37 g, 3.1 mmol), CuI (0.039 g, 0.2 mmol), L-proline (0.047 g, 0.4 mmol) and K2CO3 (0.056 g, 0.4 mmol) in DMSO (4 ml) was heated under microwave radiation to 140° C. for 1 h in a nitrogen-flushed vial. The batches were mixed and diluted with water and HCl (1 N). The resulting solution was extracted with EtOAc. The combined organic phases were washed with brine, dried and purified on flash column chromatography (isooctane/EtOAc/MeOH) to give the title compound (0.89 g). MS m/z (rel. intensity, 70 eV) 244 (M+, bp), 213 (40), 165 (27), 134 (22), 79 (18).

Fuente