Dimethyl Sulfoxide → 1-(2-phenylcyclopropyl)ethanone

HRID 1244120Notes

Reaction equation

HRID 1244120 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

HCID 2342351-(2-phenylcyclopropyl)ethanoneYield 97%

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-e8a9b5d69a82442b9e2b573b0de29def
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

Loading…