反応 #10276

反応方程式

sodium periodate

1-pent-4-enyl-azocan-2-one

→

4-(2-oxo-azocan-1-yl)-butyraldehyde

溶媒

tetrahydrofuran

water

反応条件

後処理

1. 1
   温度cooling
2. 2
   workup.STIRRINGThe reaction mixture was stirred for 3 hours
3. 3
   ろ過filtered
4. 4
   濃縮The filtrate was concentrated, saturated with solid sodium chloride
5. 5
   抽出extracted with methylene chloride
6. 6
   乾燥The organic phase was dried (magnesium sulfate)
7. 7
   濃縮concentrated
8. 8
   その他Purification by silica gel chromatography
9. 9
   洗浄eluting with chloroform

実験手順

Osmium tetroxide (17 mg, 0.07 mmole) was added to 1-pent-4-enyl-azocan-2-one (5.52 g, 28.3 mmole) in a mixture of tetrahydrofuran (100 mL) and water (50 mL) under ambient water bath cooling. The mixture was stirred for 5 minutes and solid sodium periodate (15.11 g, 70.65 mmole) was added in portions over 15 minutes. The reaction mixture was stirred for 3 hours and filtered. The filtrate was concentrated, saturated with solid sodium chloride, and extracted with methylene chloride. The organic phase was dried (magnesium sulfate) and concentrated. Purification by silica gel chromatography, eluting with chloroform, gave 4-(2-oxo-azocan-1-yl)-butyraldehyde (4.72 μg).

出典