HCID 58557499, compound → HCID 58557754, compound

HRID 1969546Notes

Reaction equation

HRID 1969546 reaction equation
[CH2:1]([CH:3]1[CH2:7][CH:6]([CH2:8][OH:9])[CH2:5][CH:4]1[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH2:1]([CH:3]1[CH2:7][CH:6]([CH:8]=[O:9])[CH2:5][CH:4]1[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:2]

Participants

4

Reactant 2

HCID 58557499HCID 58557499, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 58557754HCID 58557754, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of ethyl 2-ethyl-4-(hydroxymethyl)cyclopentanecarboxylate (4.84 g, 24.2 mmol) in DCM (100 mL) was added pyridinium chlorochromate (10.42 g, 48.3 mmol). The reaction mixture was stirred at about 25° C. for about 3 h. Silica gel (1 g) was added. The mixture was stirred at about 25° C. for about 30 min. The solid was removed by vacuum filtration, while rinsing with DCM (100 mL). The filtrate was concd under reduced pressure. The resulting residue was purified using silica gel chromatography eluting with a gradient of 0-40% EtOAc/Heptane to give ethyl 2-ethyl-4-formylcyclopentanecarboxylate (3.03 g, 63%) as a clear oil: 1H NMR (DMSO-d6) δ 9.66-9.47 (m, 1H), 4.12-3.94 (m, 2H), 2.94-2.73 (m, 2H), 2.19-1.90 (m, 4H), 1.55-1.65 (m, 1H), 1.37-1.23 (m, 1H), 1.23-1.06 (m, 4H), 0.96-0.82 (m, 3H).

Workup

  1. additionSilica gel (1 g) was added
  2. stirringThe mixture was stirred at about 25° C. for about 30 min
  3. customThe solid was removed by vacuum filtration
  4. washwhile rinsing with DCM (100 mL)
  5. customThe resulting residue was purified
  6. washeluting with a gradient of 0-40% EtOAc/Heptane

Sources & evidence

ORD record
ord-a39bf346e38249deb52a3c2882799f44
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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