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

HRID 928092노트

반응식

HRID 928092 반응식
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]

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 6093376Ruthenium trichloride hydrate촉매HCID 5943Carbon Tetrachloride용매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

(−)-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.

후처리

  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

출처 및 근거

ORD 기록
ord-2adc0166c7544afcb596841ba4d6ff9c
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290490B2

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