Réaction #67263

Équation de réaction

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

sodium methanesulfinate

L-proline

K2CO3

→

title compound

Rendement 182.2%

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

Rendement 182.2%

Solvants

DMSO

Conditions de réaction

Traitement

1. 1
   Autreflushed vial
2. 2
   workup.ADDITIONThe batches were mixed
3. 3
   workup.ADDITIONdiluted with water and HCl (1 N)
4. 4
   ExtractionThe resulting solution was extracted with EtOAc
5. 5
   LavageThe combined organic phases were washed with brine
6. 6
   Autredried
7. 7
   Autrepurified on flash column chromatography (isooctane/EtOAc/MeOH)

Mode opératoire

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).

Source