3-Oxocyclobutane-1-carboxylic acid → Ethyl 3-oxocyclobutanecarboxylate

HRID 2242209Notes

Reaction equation

HRID 2242209 reaction equation
[O:1]=[C:2]1[CH2:5][CH:4]([C:6]([OH:8])=[O:7])[CH2:3]1.[CH2:9](C(CC)(CC)C([O-])([O-])[O-])[CH3:10]>C1(C)C=CC=CC=1>[CH2:9]([O:7][C:6]([CH:4]1[CH2:5][C:2](=[O:1])[CH2:3]1)=[O:8])[CH3:10]

Participants

4

Reactant 2

HCID 49133583-Oxocyclobutane-1-carboxylic acidHCID 21875354Triethylorthoaceate

Product 1

HCID 22467070Ethyl 3-oxocyclobutanecarboxylateYield 87.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-oxo-cyclobutanecarboxylic acid (6.0 g, 52.4 mmol; J. Org. Chem. 1988 53, 3841-3843), triethylorthoacetate (28.8 mL, 157 mmol) and toluene (120 mL) was heated at 110° C. for 5 hours. The reaction mixture was cooled to room temperature and quenched with 1.0 N HCl (120 mL). The organic phase was separated, washed with a saturated NaHCO3 and brine, dried (Na2SO4), filtered and concentrated in vacuo to provide the title compound (6.5 g, 80% yield) as an oil.

Workup

  1. customquenched with 1.0 N HCl (120 mL)
  2. customThe organic phase was separated
  3. washwashed with a saturated NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40ae5a058bab484f84c27f07b5dde338
Source dataset
uspto-grants-2010_03
Patent number
US07671043B2

Reaction notes

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