반응 #67268

반응 방정식

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

sodium methanesulfinate

L-proline

K2CO3

→

title compound

수율 78.2%

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

수율 78.2%

용매

DMSO

반응 조건

후처리

1. 1
   기타flushed vials
2. 2
   workup.ADDITIONWater and EtOAc were added
3. 3
   추출The water layer was extracted with EtOAc (3×100 ml)
4. 4
   세척the combined organic phases were washed with LiCl (5%), HCl (1 N) and brine
5. 5
   건조The resulting solution was dried (Na2SO4)
6. 6
   기타evaporated to dryness
7. 7
   기타The residue was purified by flash column chromatography (isooctane/EtOAc)

실험 절차

Two batches of [(2R)-7-bromo-2,3-dihydro-1,4-benzodioxin-2-yl]methanol (2.2 g, 8.9 mmol), sodium methanesulfinate (85%) (1.6 g, 13.3 mmol), CuI (0.2 g, 0.9 mmol), L-proline (0.2 g, 1.8 mmol) and K2CO3 (0.2 g, 1.8 mmol) in DMSO (20 ml) were heated under microwave radiation at 140° C. for 3 h in nitrogen-flushed vials. Water and EtOAc were added. The water layer was extracted with EtOAc (3×100 ml) and the combined organic phases were washed with LiCl (5%), HCl (1 N) and brine. The resulting solution was dried (Na2SO4) and evaporated to dryness. The residue was purified by flash column chromatography (isooctane/EtOAc) to give the title compound (1.7 g). MS m/z (rel. intensity, 70 eV) 244 (M+, bp), 213 (39), 165 (26), 134 (22), 79 (23).

출처