Hexane → HCID 131721845, compound

HRID 1421131Notes

Reaction equation

HRID 1421131 reaction equation
C([Li])CCC.CCCCCC.[CH:12]1([C:18]2([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:22]=[CH:21][CH:20]=[CH:19]2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.S(C1C=CC(C)=CC=1)(O[CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])(=O)=O>O1CCCC1.O>[CH3:36][N:35]([CH2:34][CH2:33][C:19]1[C:18]([CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)([CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[CH:22]=[CH:21][CH:20]=1)[CH3:37]

Participants

7

Reactant 4

HCID 8058HexaneHCID 109557742-(dimethylamino)ethyl 4-methylbenzenesulfonateHCID 131721844HCID 131721844, compoundHCID 178418339Butyllithium

Product 1

HCID 131721845HCID 131721845, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, a solution of n-butyllithium in hexane (18.7 mL; 1.6 mol/L; 30 mmol) was added dropwise to a cooled (0° C.) solution of dicyclohexyl-cyclopentadiene (Example IV) (6.90 g; 30.0 mmol) in dry tetrahydrofuran (125 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, 30.0 mmol of 2-dimethylaminoethyl tosylate prepared in situ were added. After 18 hours of stirring, the conversion was found to be 88%, 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 evaporated to dryness. The residue was purified on a silica gel column, which resulted in 7.4 g of (dimethylaminoethyl)dicyclohexylcyclo-pentadiene.

Workup

  1. customprovided with a magnetic stirrer and a dropping funnel
  2. additionwere added
  3. stirringAfter 18 hours of stirring
  4. additionwas carefully added dropwise to the reaction mixture
  5. distillationthe tetrahydrofuran was then distilled off
  6. extractionThe crude product was extracted with ether
  7. dry with materialthe combined organic phase was then dried with sodium sulphate
  8. customevaporated to dryness
  9. customThe residue was purified on a silica gel column, which
  10. customresulted in 7.4 g of (dimethylaminoethyl)dicyclohexylcyclo-pentadiene

Sources & evidence

ORD record
ord-09258765b5214fdba944e3d7e8044ee1
Source dataset
uspto-grants-2000_06
Patent number
US06072067

Reaction notes

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