反応 #2254195

反応方程式

pyridinium dichromate

9-methoxy-nonanol

sodium acetate

→

9-methoxy-nonanal

収率 54.4%

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他a 50-mL, one-necked, round-bottom flask equipped with a magnetic stirrer
2. 2
   workup.STIRRINGThe reaction mixture was stirred at room temperature under nitrogen for 5 minutes
3. 3
   workup.STIRRINGstirred overnight
4. 4
   その他The progress of reaction
5. 5
   その他After completion of the reaction
6. 6
   ろ過the reaction mixture was filtered through a bed of silica gel (˜15 g)
7. 7
   その他The filtrate was evaporated in vacuo
8. 8
   その他to obtain a crude compound
9. 9
   その他This was purified by column chromatography
10. 10
    洗浄to elute the product from the column
11. 11
    workup.ADDITIONAll fractions containing the desired pure product
12. 12
    濃縮concentrated in vacuo

実験手順

a 50-mL, one-necked, round-bottom flask equipped with a magnetic stirrer and stir bar was charged with 9-methoxy-nonanol (1.0 g, 5.9 mmol), dichloromethane (10 mL), molecular sieves (1.0 g, 3 A), sodium acetate (0.1 g) at room temperature. The reaction mixture was stirred at room temperature under nitrogen for 5 minutes. The reaction mixture was charged with pyridinium dichromate (4.7 g, 12.5 mmol) and stirred overnight. The progress of reaction was monitored by TLC (Note 1). After completion of the reaction, the reaction mixture was filtered through a bed of silica gel (˜15 g). The filtrate was evaporated in vacuo to obtain a crude compound. This was purified by column chromatography using silica gel column (250-400 mesh, 40 g). A solvent gradient of ethyl acetate in hexane (10-50%) was used to elute the product from the column. All fractions containing the desired pure product were combined and concentrated in vacuo to give pure 9-methoxy-nonanal (lot D-1027-156, 553 mg, 54.4%). Completion of the reaction was monitored by thin layer chromatography (TLC) using a thin layer silica gel plate; eluent: 60% ethyl acetate in hexanes.

出典