反应 #50685

反应方程式

potassium hydroxide

3-benzoylpyrrole

Hydroxylamine-O-sulfonic acid

→

desired product

(1-Amino-1H-pyrrol-3-yl)phenylmethanone

溶剂

water

dimethylformamide

反应条件

后处理

1. 1
   workup.ADDITIONAfter the addition
2. 2
   workup.STIRRINGwas stirred for 30 minutes at room temperature
3. 3
   萃取extracted with DCM
4. 4
   洗涤The combined organic layers were washed with water
5. 5
   干燥dried over magnesium sulfate
6. 6
   其他evaporated in vacuo
7. 7
   其他The residue was purified by flash column chromatography (silica gel, DCM/ethyl acetate, 5:1)
8. 8
   其他affording

实验过程

To a solution of 3-benzoylpyrrole (4.92 g) in 50 ml of dry dimethylformamide was added milled potassium hydroxide (8.06 g). Hydroxylamine-O-sulfonic acid (4.23 g) was added to the suspension in 4 portions over a period of 1 hour with stirring at room temperature. After the addition was completed the reaction mixture was stirred for 30 minutes at room temperature, and subsequently diluted with 50 ml of water and extracted with DCM. The combined organic layers were washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography (silica gel, DCM/ethyl acetate, 5:1), affording starting material (1.44 g) and the desired product as the second fraction. Recrystallization from ethyl ether/hexane gave the product as crystals (1.80 g), which was combined with material obtained from a 36.9 mmol scale reaction and recrystallized from DCM/hexane affording 3.20 g of crystals, m.p. 82°-83° C.

来源