Water → (1r,3s)-3-Acetyl-2,2-dimethylcyclobutane-1-carboxylic acid

HRID 928092ノート

反応式

HRID 928092 の反応式
C[C:2]1[CH:8]2[C:9]([CH3:11])([CH3:10])[CH:6]([CH2:7]2)[C:4](=[O:5])[CH:3]=1.I([O-])(=O)(=O)=[O:13].[Na+].[OH2:18]>C(#N)C.C(Cl)(Cl)(Cl)Cl.C(Cl)Cl.O.[Ru](Cl)(Cl)Cl>[C:2]([C@H:8]1[CH2:7][C@@H:6]([C:4]([OH:13])=[O:5])[C:9]1([CH3:11])[CH3:10])(=[O:18])[CH3:3]

参加物

8

反応物 3

HCID 962WaterHCID 290254,6,6-Trimethylbicyclo(3.1.1)hept-3-en-2-oneHCID 23667635Sodium periodate

生成物 1

HCID 11008353(1r,3s)-3-Acetyl-2,2-dimethylcyclobutane-1-carboxylic acid

試薬・触媒・溶媒 4

HCID 6093376Ruthenium trichloride hydrate触媒HCID 5943Carbon Tetrachloride溶媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

(−)-Verbenone (615 mg, 4.09 mmol) was dissolved in a mixture of acetonitrile (2.0 mL), CCl4 (2.0 mL) and water (3.0 mL). Sodium periodate (3.59 g, 16.79 mmol) and ruthenium(III) chloride hydrate (18.68 mg, 0.090 mmol) were added and the resulting biphasic mixture was stirred vigorously at room temperature for 24 hrs. The reaction mixture was then diluted with DCM, washed with H2O and extracted with DCM (3×). The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure to give (1R,3S)-3-acetyl-2,2-dimethylcyclobutanecarboxylic acid as a pale yellow oil, which was used without further purification. MS ESI calc'd. for C9H15O3 [M+H]+ 171. found 171.

後処理

  1. washwashed with H2O
  2. extractionextracted with DCM (3×)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-2adc0166c7544afcb596841ba4d6ff9c
出典データセット
uspto-grants-2016_03
特許番号
US09290490B2

反応ノート

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