Sodium hydride → HCID 67086633, compound

HRID 1807407Notes

Reaction equation

HRID 1807407 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[Cl:9][C:10]1[S:11][C:12]([Cl:21])=[C:13]([Cl:20])[C:14]=1/[CH:15]=[CH:16]/[C:17](=[O:19])[CH3:18]>CS(C)=O.[Cl-].[Na+].O>[Cl:9][C:10]1[S:11][C:12]([Cl:21])=[C:13]([Cl:20])[C:14]=1[C@@H:15]1[CH2:4][C@H:16]1[C:17](=[O:19])[CH3:18]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 67086773HCID 67086773, compound

Product 1

HCID 67086633HCID 67086633, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred mixture of solid sodium hydride (55-65% in oil; 1.5 g; 34 mmol) and trimethylsulfoxonium iodide (7.6 g; 34 mmol) under nitrogen was added in one portion a solution of (E)-4-(2,4,5-Trichloro-thiophen-3-yl)-but-3-en-2-one (7.0 g; 27 mmol) prepared as described in example P33 in dry dimethylsulfoxide (300 mL). The reaction is slightly exothermic and gas evolution is observed. The reaction mixture was stirred for 10 minutes at ambient temperature then poured on water (600 ml) and brine (100 ml) then extracted with dichloromethane (3×300 ml). Combined organic layers were washed with water (2×800 ml) and dried over anhydrous sodium sulphate. The solvent was removed in vacuo and the residue was purified by chromatography over silica gel (eluant: cyclohexane/ethyl acetate 90:10) to afford 2.7 g (37% of theory) of trans-1-[2-(2,4,5-trichloro-thiophen-3-yl)-cyclopropyl]-ethanone as a yellow oil.

Workup

  1. customprepared
  2. extractionthen extracted with dichloromethane (3×300 ml)
  3. washCombined organic layers were washed with water (2×800 ml)
  4. dry with materialdried over anhydrous sodium sulphate
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by chromatography over silica gel (eluant: cyclohexane/ethyl acetate 90:10)

Sources & evidence

ORD record
ord-0a5e9fa9208540a88f7588d873a27973
Source dataset
uspto-grants-2013_01
Patent number
US08357635B2

Reaction notes

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