Sodium Hydroxide → HCID 124399918, compound

HRID 1807404Notes

Reaction equation

HRID 1807404 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[OH-].[Na+].[Cl:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1/[CH:17]=[CH:18]/[C:19](=[O:21])[CH3:20]>CS(C)=O>[Cl:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[C@@H:17]1[CH2:2][C@H:18]1[C:19](=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 5849647HCID 5849647, compound

Product 1

HCID 124399918HCID 124399918, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A round bottom flask equipped with magnetic stirrer, nitrogen inlet and additional funnel was charged with trimethylsulfoxonium iodide (0.61 g, 2.78 mmol), DMSO (10 ml) and powdered sodium hydroxide (97 mg, 2.44 mmol). The suspension was stirred for 1.0 hour at ambient temperature to yield a solution. So prepared solution was added drop wise at ambient temperature to a solution of (E)-4-(2,4-dichloro-phenyl)-but-3-en-2-one (0.50 g, 2.32 mmol) prepared as described in example P30 in DMSO (10 ml). The reaction mixture was stirred for 0.5 hours, poured onto ice water (100 ml) and extracted with ether (3×25 ml). Combined organic layers were washed with water, brine and dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by flash chromatography over silica gel (25 g) (eluent: n-hexane/ethyl acetate 10:1) to afford 0.33 g (62% of theory) of trans 1-[2-(2,4-dichloro-phenyl)-cyclopropyl]-ethyanone in form of an oil.

Workup

  1. customA round bottom flask equipped with magnetic stirrer, nitrogen inlet and additional funnel
  2. customto yield a solution
  3. customSo prepared solution
  4. customprepared
  5. stirringThe reaction mixture was stirred for 0.5 hours
  6. additionpoured onto ice water (100 ml)
  7. extractionextracted with ether (3×25 ml)
  8. washCombined organic layers were washed with water, brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was removed in vacuo
  11. customthe residue was purified by flash chromatography over silica gel (25 g) (eluent: n-hexane/ethyl acetate 10:1)
  12. customto afford 0.33 g (62% of theory) of trans 1-[2-(2,4-dichloro-phenyl)-cyclopropyl]-ethyanone in form of an oil

Sources & evidence

ORD record
ord-2d98c99f9f5c409eacffb117f2ee8412
Source dataset
uspto-grants-2013_01
Patent number
US08357635B2

Reaction notes

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