Ozone → Tert-Butyl 1-(2-oxoethyl)cyclopropanecarboxylate

HRID 501347Notes

Reaction equation

HRID 501347 reaction equation
[C:1]([O:5][C:6]([C:8]1([CH2:11][CH:12]=C)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:14]=[O+][O-]>CO.ClCCl>[C:1]([O:5][C:6]([C:8]1([CH2:11][CH:12]=[O:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 24823OzoneHCID 546367Cyclopropanecarboxylic acid, 1-(2-propenyl)-, 1,1-dimethylethyl ester

Product 1

HCID 58817571Tert-Butyl 1-(2-oxoethyl)cyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5.7 g (31.3 mmol) of 1-allyl-cyclopropanecarboxylic acid tert-butyl ester in 50 mL methanol and 50 mL dichloromethane under nitrogen was taken to −78° C. where ozone was bubbled in for 1 hour. Nitrogen was bubbled in until the familiar blue color dissipated. Three drops of pyridine followed by 2 mL of dimethyl sulfide were added and the cooling bath removed. After 2 hours the reaction was poured into aqueous saturated ammonium chloride solution, extracted with dichloromethane, dried and concentrated to deliver a quantitative yield of the desired aldehyde as an oil.

Workup

  1. customwas taken to −78° C.
  2. customwas bubbled in for 1 hour
  3. customNitrogen was bubbled in until the familiar blue color
  4. additionwere added
  5. customthe cooling bath removed
  6. additionAfter 2 hours the reaction was poured into aqueous saturated ammonium chloride solution
  7. extractionextracted with dichloromethane
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-937f059d688e46109fc95f29f5c72dd9
Source dataset
uspto-grants-2010_08
Patent number
US07772252B2

Reaction notes

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