反应 #463544

反应方程式

potassium

5-bromo-2-hydroxypyridine

epoxide

(5R)-4-methyl-4-(2,2,2-trifluoroethyl)-5-(4-methylsulfonyl-phenyl)-3,6-dioxabicyclo[3.1.0]hexan-2-one

5-bromo-2-hydroxypyridine

KOH

→

(5R)-3-(5-bromo-2-pyridyloxy)-4-(4-methylsulfonylphenyl)-5-methyl-5-(2,2,2-trifluoroethyl)-5H-furan-2-one

溶剂

dimethylformamide

isopropanol

反应条件

后处理

1. 1
   其他followed by evaporation to dryness with toluene and high vacuum
2. 2
   其他drying
3. 3
   温度(0.742 g, 3.5 mmol) and the mixture was warmed up slowly
4. 4
   温度to reflux for 16 hrs
5. 5
   workup.ADDITIONpoured on icy dilute ammonium chloride and ethyl acetate
6. 6
   其他the organic layer was separated
7. 7
   洗涤The combined organic layers were washed with brine
8. 8
   干燥dried with MgSO4
9. 9
   其他the solvents were removed in vacuo
10. 10
    其他to yield
11. 11
    其他after purification on silica gel (10% acetone/toluene) the title compound (0.380 g)

实验过程

To a 0° C. mixture of the epoxide(0.930 g) from step 1 in dimethylformamide(3 mL) and isopropanol(12 mL) was added the potassium salt of 5-bromo-2-hydroxypyridine, prepared from 5-bromo-2-hydroxypyridine and one equivalent of 8N KOH followed by evaporation to dryness with toluene and high vacuum drying, (0.742 g, 3.5 mmol) and the mixture was warmed up slowly to reflux for 16 hrs. It was then cooled to room temperature and poured on icy dilute ammonium chloride and ethyl acetate; the organic layer was separated and the aqueous further extracted ounce with ethyl acetate. The combined organic layers were washed with brine, dried with MgSO4 and the solvents were removed in vacuo to yield after purification on silica gel (10% acetone/toluene) the title compound (0.380 g).

来源