Chloroacetone → HCID 60204538, compound

HRID 507631Notes

Reaction equation

HRID 507631 reaction equation
Cl[CH2:2][C:3](=[O:5])[CH3:4].C(=O)([O-])[O-].[K+].[K+].[C:12]([CH:14]([C:25]([C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)=O)[C:15]([S:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)=[S:16])#[N:13]>CN(C=O)C.CCOCC.O>[C:3]([C:2]1[S:16][C:15]([S:17][C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)=[C:14]([C:12]#[N:13])[C:25]=1[C:27]1[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=1)(=[O:5])[CH3:4]

Participants

7

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 57428852HCID 57428852, compound

Product 1

HCID 60204538HCID 60204538, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Chloroacetone (0.100 mL, 1.26 mmol) was added dropwise to a stirred suspension of potassium carbonate (0.210 g, 1.52 mmol) and 4-fluorophenyl 2-cyano-3-(4-fluorophenyl)-3-oxopropanedithioate (0.20 g, 0.60 mmol) from step (ii) in DMF (2.5 mL). The reaction temperature was raised to 50° C. for 50 min. The reaction mixture was then diluted with Et2O and H2O. The organic layer was separated and washed with H2O and brine, dried over Na2SO4, and concentrated. The residue was purified by flash chromatography, eluting with a gradient of 0.75-15% EtOAc/hexanes to afford the product as a yellow oil (102 mg, 0.27 mmol, 46% yield). MS (M-H)− 370.

Workup

  1. customThe organic layer was separated
  2. washwashed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with a gradient of 0.75-15% EtOAc/hexanes

Sources & evidence

ORD record
ord-f0a4c6d074264f73be450861b812c3dd
Source dataset
uspto-grants-2010_08
Patent number
US07786132B2

Reaction notes

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