Water → HCID 131721853, compound

HRID 1421137Notes

Reaction equation

HRID 1421137 reaction equation
C([Li])CCC.[CH3:6][C:7]([C:11]1([C:16]([CH3:20])([CH3:19])[CH2:17][CH3:18])[CH:15]=[CH:14][CH:13]=[CH:12]1)([CH3:10])[CH2:8][CH3:9].S(C1C=CC(C)=CC=1)(O[CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])(=O)=O.O>CCCCCC.O1CCCC1.O1CCCC1.CCCCCC>[CH3:28][N:27]([CH2:26][CH2:25][C:15]1[C:11]([C:16]([CH3:19])([CH3:20])[CH2:17][CH3:18])([C:7]([CH3:6])([CH3:10])[CH2:8][CH3:9])[CH:12]=[CH:13][CH:14]=1)[CH3:29]

Participants

8

Reactant 4

HCID 962WaterHCID 109557742-(dimethylamino)ethyl 4-methylbenzenesulfonateHCID 131721854HCID 131721854, compoundHCID 178418339Butyllithium

Product 1

HCID 131721853HCID 131721853, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 21883165Tetrahydrofuran hexaneSolvent

Procedure

Twenty-five mL of a 1.6 molar solution of n-butyllithium in hexane was added dropwise to a cooled (0° C. ) solution of di-(1,1-dimethyl-propyl)cyclopentadiene (8.25 g; 40.0 mmol) in dry tetrahydrofuran (125 ml) under a nitrogen atmosphere 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, a solution of 2-dimethylaminoethyl tosylate (40.0 mmol) prepared in situ in tetrahydrofuran/hexane was added. After 18 hours of stirring, the conversion was found to be 91%, 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 9.1 grams (82%) of (dimethyl-aminoethyl)di(1,1-dimethyl-propyl)cyclopentadiene.

Workup

  1. customprovided with a magnetic stirrer and a dropping funnel
  2. additionwas 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. customThe residue was purified on a silica gel column, which
  9. customresulted in 9.1 grams (82%) of (dimethyl-aminoethyl)di(1,1-dimethyl-propyl)cyclopentadiene

Sources & evidence

ORD record
ord-863a0f6d5fec4403a4cdec1b4f6a702e
Source dataset
uspto-grants-2000_06
Patent number
US06072067

Reaction notes

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