Diethyl Ether → HCID 18784902, compound

Participants

Reaction Steps

Preparation of methyl 2,2-diethyl-5-oxopentanoate 5 To a well stirred mixture of the hydroxyester (1.88 g, 10 mmol), NaOAc (0.82 g, 10 mmol), and celite (1.88 g) in dry CH2Cl2 (50 mL), was added pyridinium chlorochromate (3.24 g, 15 mmol) at 0° C. in a nitrogen atmosphere. After 30 min at 0° C., the dark reaction mixture was stirred at room temperature for 2.5 h, and 100 mL of ether was added to it. Then it was filtered through a plug of silica gel and the solvent removed in vacuo to give 2.00 g of colorless viscous liquid. Column chromatography over silica gel (hexanes-EtOAc, 9:1) afforded the aldehyde (1.45 g, 78%) as a colorless liquid.

Provenance & Evidence