Water → HCID 131721851, compound

HRID 1421136Notes

Reaction equation

HRID 1421136 reaction equation
C([Li])CCC.[C:6]1([CH:12]([CH3:28])[CH2:13][C:14]2([CH2:19][CH:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH3:21])[CH:18]=[CH:17][CH:16]=[CH:15]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.S(C1C=CC(C)=CC=1)(O[CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])(=O)=O.O>CCCCCC.O1CCCC1.O1CCCC1.CCCCCC>[CH3:36][N:35]([CH2:34][CH2:33][C:15]1[C:14]([CH2:19][CH:20]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH3:21])([CH2:13][CH:12]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH3:28])[CH:18]=[CH:17][CH:16]=1)[CH3:37]

Participants

8

Reactant 4

HCID 962WaterHCID 109557742-(dimethylamino)ethyl 4-methylbenzenesulfonateHCID 131721852HCID 131721852, compoundHCID 178418339Butyllithium

Product 1

HCID 131721851HCID 131721851, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 21883165Tetrahydrofuran hexaneSolvent

Procedure

12.5 mL of a 1.6 molar solution of n-butyllithium in hexane was added dropwise to a cooled (0° C.) solution of di-(2-phenyl-propyl)-cyclopentadiene (6.05 g; 20.0 mmol) in dry tetrahydrofuran (100 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 (20.0 mmol) prepared in situ in tetrahydrofuran/hexane was added. After 18 hours of stirring, the conversion was found to be 90%, 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 5.98 grams (80%) of (dimethyl-aminoethyl)di(2-phenyl-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 5.98 grams (80%) of (dimethyl-aminoethyl)di(2-phenyl-propyl)cyclopentadiene

Sources & evidence

ORD record
ord-6272f8fdf7534a0d9710c8efdd721fad
Source dataset
uspto-grants-2000_06
Patent number
US06072067

Reaction notes

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