Sodium hydride → 1-(4-Chlorophenyl)-1-t-butyl-ethylene oxide

HRID 1638489Notes

Reaction equation

HRID 1638489 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[C:9]([C:13]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)=[O:14])([CH3:12])([CH3:11])[CH3:10]>CS(C)=O>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]2([C:9]([CH3:12])([CH3:10])[CH3:11])[O:14][CH2:4]2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 111380501-(4-Chlorophenyl)-2,2-dimethylpropan-1-one

Product 1

HCID 139839361-(4-Chlorophenyl)-1-t-butyl-ethylene oxideYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of dimethyl oxosulphonium methylide was prepared under nitrogen from sodium hydride (0.03 mol) and powdered trimethyl oxosulphonium iodide (0.03 mol) in dry dimethyl sulphoxide (40 ml). A solution of 4-chlorophenyl tertiary butyl ketone (0.025 mol) in dry dimethyl sulphoxide (10 ml) was added dropwise at room temperature and the solution heated at 50° C. for 2.5 hours. After cooling to room temperature the solution was extracted with ether (150 ml), washed with water and dried over anhydrous sodium sulphate. Removal of the solvent gave 1-(4-chlorophenyl)-1-t-butyl-ethylene oxide (95%) as a colourless liquid.

Workup

  1. temperatureAfter cooling to room temperature the solution
  2. extractionwas extracted with ether (150 ml)
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-e6f47e3038c742aa800f74aac403d0f2
Source dataset
uspto-grants-1989_11
Patent number
US04880457

Reaction notes

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