Diethyl Ether → Methyl 2-ethyl-5-oxopentanoate

HRID 330602Notes

Reaction equation

HRID 330602 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH2:12]([CH:14]([CH2:19][CH2:20][CH2:21][OH:22])[C:15]([O:17][CH3:18])=[O:16])[CH3:13].CCOCC>ClCCl>[CH2:12]([CH:14]([CH2:19][CH2:20][CH:21]=[O:22])[C:15]([O:17][CH3:18])=[O:16])[CH3:13]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14380639Methyl 2-ethyl-5-hydroxyvalerateHCID 178418287HCID 178418287, compound

Product 1

HCID 10997312Methyl 2-ethyl-5-oxopentanoateYield 59,323.102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
20 °C

Procedure

To 50.46 g (0.234 mmol) of pyridinium chlorochromate, under argon, was added 100 mL of dichloromethane followed, with rapid stirring, by 25.0 g (0.156 mmol) of methyl 2-ethyl-5-hydroxypentanoate in 20 mL of dichloromethane. After stirring at 20° C. for 2.5 h, 15 g of silica gel was added followed by 200 mL of ether. Filtration through a 3.5×40 cm silica gel column (60-200 mesh), eluting with ether and concentration at 40° C. under vacuum gave an oil, which was redissolved in 100 mL of dichloromethane. Washing with 3×100 mL of cold 1N HCl, 3×100 mL of satd. NaHCO3, drying over MgSO4, filtration, concentration at 40° C. and distillation gave methyl 2-ethyl-5-oxopentanoate 14.64 g (59%) product, b.p 104°-105° C. (16 mm Hg).

Workup

  1. addition15 g of silica gel was added
  2. filtrationFiltration through a 3.5×40 cm silica gel column (60-200 mesh)
  3. washeluting with ether and concentration at 40° C. under vacuum
  4. customgave an oil, which
  5. washWashing with 3×100 mL of cold 1N HCl, 3×100 mL of satd
  6. dry with materialNaHCO3, drying over MgSO4, filtration, concentration at 40° C.
  7. distillationdistillation

Sources & evidence

ORD record
ord-1e7f6b8b24394cdf9d5c2f4e551ee87e
Source dataset
uspto-grants-1990_01
Patent number
US04897477

Reaction notes

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