Ethyl 1-(hydroxymethyl)cyclobutane-1-carboxylate → Ethyl 1-formylcyclobutanecarboxylate

HRID 2103059Notes

Reaction equation

HRID 2103059 reaction equation
[OH:1][CH2:2][C:3]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5][CH2:4]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH:2]([C:3]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5][CH2:4]1)=[O:1]

Participants

4

Reactant 2

HCID 15670506Ethyl 1-(hydroxymethyl)cyclobutane-1-carboxylateHCID 178418287HCID 178418287, compound

Product 1

HCID 12226109Ethyl 1-formylcyclobutanecarboxylateYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane (250 mL) solution of ethyl 1-(hydroxymethyl)cyclobutanecarboxylate (12 g) at room temperature, was added a mixture of pyridinium chlorochromate (PCC) (24.5 g) and 20 g SiO2. After 17.5 h, the organic solvent was decanted, and more dichloromethane and ethylacetate were added to wash the SiO2. The combined organic phases were concentrated, the residue and the SiO2 used in the reaction were loaded onto a column and eluted with EtOAc/DCM, 0-17%, to afford ethyl 1-formylcyclobutanecarboxylate (10.2 g) as a clear oil 1H-NMR (300 MHz, CDCl3): δ=9.76 (s, 1H); 4.32-4.0751 (d, 2H); 2.7145-2.2827 (t, 4H); 2.1954-1.6632 (m, 2H); 1.4254-1.0664(t, 3H) ppm. 13C-NMR (75 MHz, CDCl3) δ=196.96, 171.7, 61.54, 57.2, 25.95, 15.64, 14.17 ppm.

Workup

  1. customthe organic solvent was decanted
  2. additionmore dichloromethane and ethylacetate were added
  3. washto wash the SiO2
  4. concentrationThe combined organic phases were concentrated
  5. washeluted with EtOAc/DCM, 0-17%

Sources & evidence

ORD record
ord-91794611292b4dd881f65338f08167bc
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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