Styrene → 2-Chloro-1-(4,5-dihydro-5-phenyl-3-isoxazolyl)ethanone

HRID 1528527Notes

Reaction equation

HRID 1528527 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+].[Cl:14][CH2:15][C:16](=[O:21])[C:17](Cl)=[N:18][OH:19]>C(#N)C>[Cl:14][CH2:15][C:16]([C:17]1[CH2:1][CH:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[O:19][N:18]=1)=[O:21]

Participants

5

Reactant 3

HCID 7501StyreneHCID 516892Sodium BicarbonateHCID 68330913-chloro-N-hydroxy-2-oxopropanimidoyl chloride2×

Product 1

HCID 866312462-Chloro-1-(4,5-dihydro-5-phenyl-3-isoxazolyl)ethanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of styrene (6.79 g, 65.3 mmol) and sodium bicarbonate (32.1 g, powder) in acetonitrile (100 mL), 3-chloro-N-hydroxy-2-oxo-propanimidoyl chloride (i.e. the product of Example 7, Step B) (10 g, 64.1 mmol) was added in 10 portions over 20 minutes. The reaction mixture was then stirred for additional 1 h and filtered. The filtered solid was rinsed with acetonitrile, and the combined filtrates were concentrated under reduced pressure to leave an oil, which was triturated first with hexanes and then with 1-chlorobutane to give 13.6 g of the title compound as a white solid.

Workup

  1. additionwas added in 10 portions over 20 minutes
  2. filtrationfiltered
  3. washThe filtered solid was rinsed with acetonitrile
  4. concentrationthe combined filtrates were concentrated under reduced pressure
  5. customto leave an oil, which
  6. customwas triturated first with hexanes

Sources & evidence

ORD record
ord-b3f031d5e8cb45359fc68f173fe14a51
Source dataset
uspto-grants-2015_07
Patent number
US09090604B2

Reaction notes

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