Sodium Hydroxide → trans 1-[2-(2,4,6-Trichloro-phenyl)-cyclopropyl]-ethanone

HRID 1807406Notes

Reaction equation

HRID 1807406 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[OH-].[Na+].[Cl:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([Cl:17])[C:11]=1/[CH:18]=[CH:19]/[C:20](=[O:22])[CH3:21]>CS(C)=O>[Cl:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([Cl:17])[C:11]=1[C@@H:18]1[CH2:2][C@H:19]1[C:20](=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 670864784-(2,4,6-Trichlorophenyl)but-3-en-2-one

Product 1

HCID 131730172trans 1-[2-(2,4,6-Trichloro-phenyl)-cyclopropyl]-ethanone

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 (106 mg, 0.40 mmol), DMSO (2.5 ml) and powdered sodium hydroxide (0.18 mg, 0.44 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-(2,4,6-trichloro-phenyl)-but-3-en-2-one (0.10 g, 0.40 mmol) prepared as described in example P32 in DMSO (2.5 ml). The reaction mixture was stirred for 0.5 hours, poured onto ice water (10 ml) and extracted with ether (3×5 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 20:1) to afford 60 mg (57% of theory) of trans 1-[2-(2,4,6-trichloro-phenyl)-cyclopropyl]-ethyanone in form of a pale yellow liquid.

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 (10 ml)
  7. extractionextracted with ether (3×5 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 20:1)
  12. customto afford 60 mg (57% of theory) of trans 1-[2-(2,4,6-trichloro-phenyl)-cyclopropyl]-ethyanone in form of a pale yellow liquid

Sources & evidence

ORD record
ord-aa17c1b543fb4cabafc6eb8247069969
Source dataset
uspto-grants-2013_01
Patent number
US08357635B2

Reaction notes

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