Diethyl Ether → HCID 18784902, compound

HRID 1108372Notes

Reaction equation

HRID 1108372 reaction equation
[CH2:1]([C:3]([CH2:12][CH3:13])([CH2:8][CH2:9][CH:10]=[O:11])[C:4]([O:6][CH3:7])=[O:5])[CH3:2].CC([O-])=O.[Na+].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCOCC>C(Cl)Cl>[CH2:12]([C:3]([CH2:1][CH3:2])([CH2:8][CH2:9][CH2:10][OH:11])[C:4]([O:6][CH3:7])=[O:5])[CH3:13]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 517045Sodium AcetateHCID 18784909HCID 18784909, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 18784902HCID 18784902, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  1. customthe dark reaction mixture
  2. stirringwas stirred at room temperature for 2.5 h
  3. filtrationThen it was filtered through a plug of silica gel
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-0baede33997349b38c293a0018449c2e
Source dataset
uspto-grants-2000_05
Patent number
US06066666

Reaction notes

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