반응 #67273

반응 방정식

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

sodium methanesulfinate

L-proline

NaOH

→

title compound

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

용매

DMSO

반응 조건

후처리

1. 1
   기타flushed vial
2. 2
   workup.ADDITIONThe mixture was mixed with 2 other batches and water and EtOAc
3. 3
   workup.ADDITIONwas added
4. 4
   추출The solution was extracted with EtOAc (3×50 ml)
5. 5
   세척The combined organic phases were washed with LiCl (5%), HCl (1 N) and brine
6. 6
   건조The resulting solution was dried (Na2SO4)
7. 7
   기타evaporated to dryness
8. 8
   기타Purification on flash column chromatography (isooctane/EtOAc)

실험 절차

A mixture of [(2S)-7-bromo-2,3-dihydro-1,4-benzodioxin-2-yl]methanol (0.6 g, 2.3 mmol), sodium methanesulfinate (85%) (0.4 g, 3.4 mmol), CuI (0.043 g, 0.2 mmol), L-proline (0.052 g, 0.5 mmol) and NaOH (0.018 g, 0.5 mmol) in DMSO (3 ml) was heated under microwave radiation at 140° C. for 2 h 30 min in a nitrogen-flushed vial. The mixture was mixed with 2 other batches and water and EtOAc was added. The solution was extracted with EtOAc (3×50 ml). The combined organic phases were washed with LiCl (5%), HCl (1 N) and brine. The resulting solution was dried (Na2SO4) and evaporated to dryness. Purification on flash column chromatography (isooctane/EtOAc) gave the title compound (1.2 g). MS m/z (rel. intensity, 70 eV) 244 (M+, bp), 213 (39), 165 (26), 134 (22), 79 (23).

출처