تفاعل #67263

معادلة التفاعل

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

sodium methanesulfinate

L-proline

K2CO3

→

title compound

المردود 182.2%

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

المردود 182.2%

المذيبات

DMSO

ظروف التفاعل

المعالجة

1. 1
   أخرىflushed vial
2. 2
   workup.ADDITIONThe batches were mixed
3. 3
   workup.ADDITIONdiluted with water and HCl (1 N)
4. 4
   استخلاصThe resulting solution was extracted with EtOAc
5. 5
   غسيلThe combined organic phases were washed with brine
6. 6
   أخرىdried
7. 7
   أخرىpurified on flash column chromatography (isooctane/EtOAc/MeOH)

الإجراء التجريبي

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).

المصدر