Hexane → HCID 131721848, compound

HRID 1421134Notes

Reaction equation

HRID 1421134 reaction equation
C([Li])CCC.CCCCCC.[CH3:12][CH:13]([C:16]1([CH:21]([CH2:23][CH3:24])[CH3:22])[CH:20]=[CH:19][CH:18]=[CH:17]1)[CH2:14][CH3:15].S(C1C=CC(C)=CC=1)(O[CH2:29][CH2:30][N:31]([CH3:33])[CH3:32])(=O)=O>O1CCCC1.O>[CH3:32][N:31]([CH2:30][CH2:29][C:17]1[C:16]([CH:13]([CH2:14][CH3:15])[CH3:12])([CH:21]([CH2:23][CH3:24])[CH3:22])[CH:20]=[CH:19][CH:18]=1)[CH3:33]

Participants

7

Reactant 4

HCID 8058HexaneHCID 109557742-(dimethylamino)ethyl 4-methylbenzenesulfonateHCID 129692610HCID 129692610, compoundHCID 178418339Butyllithium

Product 1

HCID 131721848HCID 131721848, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, a solution of n-butyllithium in hexane (31.2 ml; 1.6 mol/L; 50 mmol) was added dropwise to a cooled (0° C.) solution of di-(2-butyl)cyclopentadiene (8.90 g; 50.0 mmol) in dry tetrahydrofuran (150 ml) in a 250 mL three-necked round-bottomed flask provided with a magnetic stirrer and a dropping funnel. After 24 hours of stirring at room temperature, the 2-dimethylaminoethyl tosylate (50.0 mmol) was added. After 18 hours of stirring the conversion was found to be 96 %, and water (100 ml) was carefully added dropwise to the reaction mixture and the tetrahydrofuran was then distilled off. The crude product was extracted with ether and the combined organic phase was then dried with sodium sulphate, and boiled down. The residue was purified on a silica gel column, which resulted in 8.5 g of (dimethylaminoethyl)-di(2-butyl)cyclopentadiene.

Workup

  1. customprovided with a magnetic stirrer and a dropping funnel
  2. stirringAfter 18 hours of stirring the conversion
  3. additionwas carefully added dropwise to the reaction mixture
  4. distillationthe tetrahydrofuran was then distilled off
  5. extractionThe crude product was extracted with ether
  6. dry with materialthe combined organic phase was then dried with sodium sulphate
  7. customThe residue was purified on a silica gel column, which
  8. customresulted in 8.5 g of (dimethylaminoethyl)-di(2-butyl)cyclopentadiene

Sources & evidence

ORD record
ord-deea665431ac43819f56a3accd970648
Source dataset
uspto-grants-2000_06
Patent number
US06072067

Reaction notes

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