4-Toluenesulfonyl chloride → HCID 18783378, compound

HRID 1953373Notes

Reaction equation

HRID 1953373 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6][CH2:7]CCCC.[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15]O.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21](S(Cl)(=O)=O)=[CH:20][CH:19]=1>C1COCC1>[CH3:12][N:13]([CH2:14][CH2:15][CH:1]1[C:2]([CH2:3][CH3:4])=[C:23]([CH2:18][CH3:28])[C:22]([CH2:6][CH3:7])=[C:21]1[CH2:20][CH3:19])[CH3:17]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 79022-(Dimethylamino)ethanolHCID 8058HexaneHCID 178418339Butyllithium

Product 1

HCID 18783378HCID 18783378, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Then a solution of n-butyllithium in hexane (5.90 ml; 1.65 mol/l; 9.74 mmol) was added dropwise to a cold solution (-78° C.) of 2-dimethylaminoethanol (0.867 g; 9.74 mmol) in THF (35 ml) in a second Schlenk vessel. After stirring for two hours at room temperature, the mixture was again cooled to -78° C. and the solid p-toluenesulphonyl chloride (1.855 g; 9.74 mmol) was added slowly. The mixture was brought to 0° C. and stirred at that temperature for 5 minutes, after which the mixture from the first Schlenk vessel was added all at once. After 16 hours, the conversion was 100%. After column chromatography, 2.6 g of (dimethylaminoethyl)tetraethylcyclopentadiene was obtained. The geminal isomers were isolated from the nongeminal isomers by converting the nongeminal isomers into their sparingly soluble potassium salt and then washing this salt with a solvent in which it does not or only sparingly dissolve.

Workup

  1. temperaturethe mixture was again cooled to -78° C.
  2. customwas brought to 0° C.
  3. stirringstirred at that temperature for 5 minutes
  4. additionafter which the mixture from the first Schlenk vessel was added all at once
  5. waitAfter 16 hours

Sources & evidence

ORD record
ord-63d1e3c3d0d946bbb7dc95986b445118
Source dataset
uspto-grants-2000_09
Patent number
US06117811

Reaction notes

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