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

HRID 456573

反応式

HRID 456573 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f4e5dc42f2ab4b1e9409f7acffadbbcb
出典データセット
uspto-grants-2007_03
特許番号
US07186724B2

関連ノート

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