Реакция #67263

Уравнение реакции

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

sodium methanesulfinate

L-proline

K2CO3

→

title compound

Выход 182.2%

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

Выход 182.2%

Растворители

DMSO

Условия реакции

Обработка

1. 1
   Другоеflushed vial
2. 2
   workup.ADDITIONThe batches were mixed
3. 3
   workup.ADDITIONdiluted with water and HCl (1 N)
4. 4
   ЭкстракцияThe resulting solution was extracted with EtOAc
5. 5
   ПромывкаThe combined organic phases were washed with brine
6. 6
   Другоеdried
7. 7
   Другоеpurified on flash column chromatography (isooctane/EtOAc/MeOH)

Методика

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).

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