Réaction #2254195

Équation de réaction

pyridinium dichromate

9-methoxy-nonanol

sodium acetate

→

9-methoxy-nonanal

Rendement 54.4%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Autrea 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
   AutreThe progress of reaction
5. 5
   AutreAfter completion of the reaction
6. 6
   Filtrationthe reaction mixture was filtered through a bed of silica gel (˜15 g)
7. 7
   AutreThe filtrate was evaporated in vacuo
8. 8
   Autreto obtain a crude compound
9. 9
   AutreThis was purified by column chromatography
10. 10
    Lavageto elute the product from the column
11. 11
    workup.ADDITIONAll fractions containing the desired pure product
12. 12
    Concentrationconcentrated in vacuo

Mode opératoire

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.

Source