반응 #2254195

반응 방정식

pyridinium dichromate

9-methoxy-nonanol

sodium acetate

→

9-methoxy-nonanal

수율 54.4%

용매

dichloromethane

반응 조건

후처리

1. 1
   기타a 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
   기타The progress of reaction
5. 5
   기타After completion of the reaction
6. 6
   여과the reaction mixture was filtered through a bed of silica gel (˜15 g)
7. 7
   기타The filtrate was evaporated in vacuo
8. 8
   기타to obtain a crude compound
9. 9
   기타This was purified by column chromatography
10. 10
    세척to elute the product from the column
11. 11
    workup.ADDITIONAll fractions containing the desired pure product
12. 12
    농축concentrated in vacuo

실험 절차

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.

출처