Dimethyl Sulfoxide → 1-(2-Phenylcyclopropyl)ethanone

HRID 1244120Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1244120
[H-].[Na+].[C:3]1([CH:9]=[CH:10][C:11](=[O:13])[CH3:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:14]S(C)=O>>[C:3]1([CH:9]2[CH2:14][CH:10]2[C:11](=[O:13])[CH3:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

4

Edukt 3

HCID 679Dimethyl SulfoxideHCID 159094-Phenyl-3-Buten-2-oneHCID 24758Sodium hydride

Produkt 1

HCID 2342351-(2-Phenylcyclopropyl)ethanoneAusbeute 97 %

Versuchsvorschrift

To Me3SOI (2.2 g, 10 mmol) in DMSO (20 mL) was added NaH (50%, 480 mg, 10 mmol). 4-Phenyl-but-3-en-2-one (1.13 g, 7.7 mmol) was added after 10 min. The reaction mixture was quenched after 30 min with water, extracted with EtOAc, and washed with water (3×30 mL). The organic extract was dried over MgSO4 and concentrated to give 1-(2-Phenyl-cyclopropyl)-ethanone (1.5 g, 97%).

Aufarbeitung

  1. customThe reaction mixture was quenched after 30 min with water
  2. extractionextracted with EtOAc
  3. washwashed with water (3×30 mL)
  4. extractionThe organic extract
  5. dry with materialwas dried over MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e8a9b5d69a82442b9e2b573b0de29def
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07119205B2

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