Hydrochloric Acid → HCID 86619564, compound

HRID 251306Notes

Reaction equation

HRID 251306 reaction equation
[CH2:1]([C:3]1[CH2:7][CH:6]=[C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:4]=1)[CH3:2].C([Li])CCC.CN1CCN(C)C1=O.[C:25]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl>CCCCCC.C1COCC1>[C:8]([C:5]1[CH:4]=[C:3]([CH2:1][CH3:2])[C:7](=[C:25]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:6]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 3102BenzophenoneHCID 66611,3-Dimethyl-2-imidazolidinoneHCID 206271323-tert-Butyl-1-ethylcyclopenta-1,3-dieneHCID 178418339Butyllithium

Product 1

HCID 86619564HCID 86619564, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A 300-ml three-necked flask equipped with a magnetic stirrer and a three-way cock in a nitrogen atmosphere was charged with 5.11 g (23.9 mmol) of 1-ethyl-3-tert-butylcyclopentadiene (GC purity: 75%) and 150 ml of THF. In a dry ice/methanol bath, 16 ml of a 1.56 M hexane solution of n-butyllithium (25.2 mmol) was slowly added dropwise. The mixture was stirred at room temperature for 20 hours, and 3.1 ml (28.8 mmol) of 1,3-dimethyl-2-imidazolidinone was added and 5.3 g (28.8 mmol) of benzophenone was further added. The mixture was stirred under reflux for 48 hours, and the resultant reaction solution was poured into 100 ml of 2N hydrochloric acid. The organic phase was separated, and the aqueous phase was extracted with 50 ml of hexane two times. The organic phases were combined and washed with a saturated aqueous sodium hydrogencarbonate solution, water and a saturated aqueous sodium chloride solution. The product was dried over magnesium sulfate and the solvent was distilled off. The distillate was purified by column chromatography to give 4.2 g of an orange solid. The yield was 56%. The compound was identified by 1H-NMR spectroscopy. The results are as follows.

Workup

  1. customA 300-ml three-necked flask equipped with a magnetic stirrer
  2. stirringThe mixture was stirred
  3. temperatureunder reflux for 48 hours
  4. customthe resultant reaction solution
  5. customThe organic phase was separated
  6. extractionthe aqueous phase was extracted with 50 ml of hexane two times
  7. washwashed with a saturated aqueous sodium hydrogencarbonate solution, water
  8. dry with materialThe product was dried over magnesium sulfate
  9. distillationthe solvent was distilled off
  10. distillationThe distillate was purified by column chromatography

Sources & evidence

ORD record
ord-bf13461419fd4812ae870e47b775e6c7
Source dataset
uspto-grants-2011_01
Patent number
US07863368B2

Reaction notes

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