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

HRID 1807405

Reaction equation

HRID 1807405 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[OH-].[Na+].[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:11]=1[CH:17]=[CH:18][C:19](=[O:21])[CH3:20]>CS(C)=O>[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[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 2777112Benzene,1,3-dichloro-2-[(2-propyn-1-yloxy)methyl]-

Product 1

HCID 69677115trans 1-[2-(2,6-Dichloro-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 (1.1 g, 5.02 mmol), DMSO (10 ml) and powdered sodium hydroxide (0.175 g, 4.39 mmol). The suspension was stirred for 1.5 hours at ambient temperature to yield a solution. So prepared solution was added drop wise at ambient temperature to a solution of 4-(2,6-dichloro-phenyl)-but-3-en-2-one (0.90 g, 4.18 mmol) prepared as described in example P31 in DMSO (5 ml). The reaction mixture was stirred for 0.5 hours, poured onto ice 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 20:1) to afford 0.30 g (31% of theory) of trans 1-[2-(2,6-dichloro-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
  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 20:1)
  12. customto afford 0.30 g (31% of theory) of trans 1-[2-(2,6-dichloro-phenyl)-cyclopropyl]-ethyanone in form of a pale yellow liquid

Sources & evidence

ORD record
ord-d43acfa999e54e89bdaf995d60e57e73
Source dataset
uspto-grants-2013_01
Patent number
US08357635B2

Linked notes

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