Hydrochloric Acid → HCID 86619564, compound

HRID 2404928Notes

Reaction equation

HRID 2404928 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

To a 300-ml three-necked flask equipped with a magnetic stirring bar and a three-way cock was charged with 5.11 g (23.9 mmol) of 1-ethyl-3-tert-butylcyclopentadiene (GC purity 75%) and 150 ml of THF under nitrogen atmosphere. To the solution was added, slowly and dropwise, 16 ml of a hexane solution of n-butyllithium (1.56 M: 25.2 mmol) in a dry ice/methanol bath, and the mixture was stirred at room temperature for 20 hours. To the resultant reaction liquid were added 3.1 ml (28.8 mmol) of 1,3-dimethyl-2-imidazolidinone and then 5.3 g (28.8 mmol) of benzophenone, and the solution was stirred under reflux for 48 hours. The reaction solution was poured into 100 ml of 2N hydrochloric acid. The organic layer was separated and the aqueous layer was subjected to extraction with 50 ml of hexane twice. The combined organic layer was washed with saturated sodium hydrogen carbonate aqueous solution, water, and saturated brine. After drying over magnesium sulfate, the solvent was distilled off. The residue was purified by column chromatography to obtain 4.2 g of an orange solid. The yield was 56%. The identification was carried out by 1H-NMR spectrum. The measurement results are shown below.

Workup

  1. customTo a 300-ml three-necked flask equipped with a magnetic stirring bar
  2. additionTo the solution was added
  3. customTo the resultant reaction liquid
  4. temperatureunder reflux for 48 hours
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was subjected to extraction with 50 ml of hexane twice
  7. washThe combined organic layer was washed with saturated sodium hydrogen carbonate aqueous solution, water, and saturated brine
  8. dry with materialAfter drying over magnesium sulfate
  9. distillationthe solvent was distilled off
  10. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-38bf3e7706c84efca506fc777e7ff4ab
Source dataset
uspto-grants-2014_08
Patent number
US08802779B2

Reaction notes

Loading…