反応 #43640

反応方程式

7-bromo-2,3-dihydro-1-benzofuran-5-carbaldehyde

copper(I) cyanide

→

desired product

収率 61.4%

5-formyl-2,3-dihydro-1-benzofuran-7-carbonitrile

収率 61.4%

溶媒

dimethylacetamide

反応条件

後処理

1. 1
   温度The reaction was refluxed for 18 hours
2. 2
   濃縮concentrated under reduced pressure
3. 3
   洗浄The residue was washed well with warm ethyl acetate
4. 4
   濃縮The combined ethyl acetate layer were concentrated
5. 5
   その他dried
6. 6
   その他The crude product was purified by flash column chromatography (silica gel, 4:1 and 2:1 hexane:ethyl acetate gradient)

実験手順

To a solution of 7-bromo-2,3-dihydro-1-benzofuran-5-carbaldehyde (1.3 g, 4.7 mmol) in dimethylacetamide (2 mL) was added copper(I) cyanide (0.41 g g, 4.7 mmol). The reaction was refluxed for 18 hours, and then concentrated under reduced pressure. The residue was washed well with warm ethyl acetate. The combined ethyl acetate layer were concentrated and dried. The crude product was purified by flash column chromatography (silica gel, 4:1 and 2:1 hexane:ethyl acetate gradient) to afford the desired product (0.5 g, 50%).

出典