Water → HCID 15501724, compound

HRID 369506Notes

Reaction equation

HRID 369506 reaction equation
C([Li])CCC.[CH3:6][CH:7]([C:9]1[C:10]([CH:17]([CH3:19])[CH3:18])=[C:11]([CH:14]([CH3:16])[CH3:15])[CH2:12][CH:13]=1)[CH3:8].S(C1C=CC(C)=CC=1)(O[CH2:24][CH2:25][N:26]([CH3:28])[CH3:27])(=O)=O.O>C1COCC1>[CH3:27][N:26]([CH2:25][CH2:24][C:13]1[CH2:12][C:11]([CH:14]([CH3:16])[CH3:15])=[C:10]([CH:17]([CH3:19])[CH3:18])[C:9]=1[CH:7]([CH3:6])[CH3:8])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 109557742-(dimethylamino)ethyl 4-methylbenzenesulfonateHCID 156679961,2,3-Tri(propan-2-yl)cyclopenta-1,3-dieneHCID 178418339Butyllithium

Product 1

HCID 15501724HCID 15501724, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a dry 500 mL three-necked flask with a magnetic stirrer, a solution of 62.5 mL of n-butyllithium (1.6M in n-hexane; 100 mmol) was added under a dry nitrogen atmosphere to a solution of 19.2 g (100 mmol) of tri-(2-propyl)cyclopentadiene in 250 mL of THF at -60° C. After heating to room temperature (in approximately 1 hour) stirring continued for a further 2 hours. After cooling to -60° C., a solution of (dimethylaminoethyl) tosylate (105 mmol) prepared in situ was added over a period of 5 minutes. The reaction mixture was heated to room temperature, followed by overnight stirring. The degree of conversion of the reaction was monitored by GC. After addition of water, the product was extracted with petroleum ether (40-60° C.). The combined organic layer was dried (Na2SO4) and evaporated under reduced pressure. The conversion was greater than 95%. 30% of the product is geminally substituted.

Workup

  1. temperatureAfter cooling to -60° C.
  2. additionwas added over a period of 5 minutes
  3. temperatureThe reaction mixture was heated to room temperature
  4. waitfollowed by overnight
  5. stirringstirring
  6. extractionthe product was extracted with petroleum ether (40-60° C.)
  7. dry with materialThe combined organic layer was dried (Na2SO4)
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-499d06a2bfcf4f5eabe6c4252d029413
Source dataset
uspto-grants-2000_10
Patent number
US06137019

Reaction notes

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