Diethyl Ether → Methyl 6-oxohexanoate

HRID 555362Notes

Reaction equation

HRID 555362 reaction equation
[C:1]([O:4][CH2:5]C)(=[O:3])[CH3:2].[CH3:7][CH2:8][CH2:9][CH2:10]CC.C([O:15]CC)C>ClCCl>[O:15]=[CH:10][CH2:9][CH2:8][CH2:7][CH2:2][C:1]([O:4][CH3:5])=[O:3]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 21226206Ethyl acetate hexane

Product 1

HCID 81164Methyl 6-oxohexanoateYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium chlorochromate (16.27 g, 75.48 mM) was dissolved in dichloromethane (140 ml), and a solution of methyl 6-hydroxy-hexanoate (10.03 g, 68.61 mM) obtained in Preparation Example 3-1 dissolved in dichloromethane (20 ml) was added dropwise thereto for 30 min. The resulting mixture was stirred at 25˜30° C. for 2 hrs. After the completion of reaction, the reaction mixture was diluted with ethyl ether, filtered and concentrated under reduced pressure. The residue thus obtained was subjected to a silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/4) to obtain 5.77 g of the title compound (yield 59%).

Workup

  1. additionwas added dropwise
  2. customAfter the completion of reaction
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained

Sources & evidence

ORD record
ord-d89deed3e70f4fae8742c84e90961961
Source dataset
uspto-grants-2011_11
Patent number
US08053435B2

Reaction notes

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