반응 #67280

반응 방정식

(7-bromo-5-fluoro-2,3-dihydro-1,4-benzodioxin-2-yl)methanol

sodium methanesulfinate

L-proline

K2CO3

→

title compound

수율 33.2%

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

수율 33.2%

용매

DMSO

반응 조건

후처리

1. 1
   기타flushed vials
2. 2
   온도After cooling to ambient temperature
3. 3
   workup.ADDITIONthe batches were mixed
4. 4
   workup.ADDITIONwater and EtOAc were added
5. 5
   추출the water phase was extracted with EtOAc
6. 6
   세척The combined organic phases were washed with LiCl (5%), HCl (1 N), brine
7. 7
   건조dried (Na2SO4)
8. 8
   기타evaporated to dryness
9. 9
   workup.ADDITIONThe product was mixed with another batch of the same compound
10. 10
    기타Purification on flash column chromatography (isooctane/EtOAc/MeOH)

실험 절차

A mixture of (7-bromo-5-fluoro-2,3-dihydro-1,4-benzodioxin-2-yl)methanol (0.6 g, 2.3 mmol), sodium methanesulfinate (85%) (0.4 g, 3.5 mmol), CuI (0.04 g, 0.2 mmol), L-proline (0.05 g, 0.5 mmol) and K2CO3 (0.06 g, 0.5 mmol) in DMSO (6 ml) was heated in two batches under microwave radiation at 140° C. for 2 h in nitrogen-flushed vials. After cooling to ambient temperature, the batches were mixed, water and EtOAc were added and the water phase was extracted with EtOAc. The combined organic phases were washed with LiCl (5%), HCl (1 N), brine, dried (Na2SO4) and evaporated to dryness. The product was mixed with another batch of the same compound. Purification on flash column chromatography (isooctane/EtOAc/MeOH) gave the title compound (0.2 g). MS m/z (rel. intensity, 70 eV) 262 (M+, bp), 231 (32), 206 (12), 183 (17), 152 (14).

출처