반응 #67263

반응 방정식

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

sodium methanesulfinate

L-proline

K2CO3

→

title compound

수율 182.2%

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

수율 182.2%

용매

DMSO

반응 조건

후처리

1. 1
   기타flushed vial
2. 2
   workup.ADDITIONThe batches were mixed
3. 3
   workup.ADDITIONdiluted with water and HCl (1 N)
4. 4
   추출The resulting solution was extracted with EtOAc
5. 5
   세척The combined organic phases were washed with brine
6. 6
   기타dried
7. 7
   기타purified on flash column chromatography (isooctane/EtOAc/MeOH)

실험 절차

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).

출처