Reaktion #2254195

Reaktionsgleichung

pyridinium dichromate

9-methoxy-nonanol

sodium acetate

→

9-methoxy-nonanal

Ausbeute 54.4%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigea 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
   SonstigeThe progress of reaction
5. 5
   SonstigeAfter completion of the reaction
6. 6
   Filtrationthe reaction mixture was filtered through a bed of silica gel (˜15 g)
7. 7
   SonstigeThe filtrate was evaporated in vacuo
8. 8
   Sonstigeto obtain a crude compound
9. 9
   SonstigeThis was purified by column chromatography
10. 10
    Waschento elute the product from the column
11. 11
    workup.ADDITIONAll fractions containing the desired pure product
12. 12
    Einengenconcentrated in vacuo

Vorschrift

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.

Quelle