Hydrochloric Acid → HCID 86619564, compound

HRID 423128Notes

Reaction equation

HRID 423128 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].CCCCCC.C([Li])CCC.CN1CCN(C)C1=O.[C:31]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)(=O)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.Cl>C1COCC1>[C:8]([C:5]1[CH:4]=[C:3]([CH2:1][CH3:2])[C:7](=[C:31]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:6]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3102BenzophenoneHCID 66611,3-Dimethyl-2-imidazolidinoneHCID 206271323-tert-Butyl-1-ethylcyclopenta-1,3-dieneHCID 178418244HCID 178418244, compound

Product 1

HCID 86619564HCID 86619564, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 300 ml three neck flask equipped with a magnetic stirrer and a three-way cock was charged with 5.11 g (23.9 mmol) (GC purity: 75%) of 1-ethyl-3-tert-butylcyclopentadiene and 150 ml of THF under nitrogen atmosphere. A 1.56M n-butyllithium hexane solution 16 ml (25.2 mmol) was added dropwise thereto on a dry ice/methanol bath, and then the solution was stirred at room temperature for 20 hours. 1,3-Dimethyl-2-imidazolidinone 3.1 ml (28.8 mmol) was added to the reaction solution obtained, and subsequently 5.3 g (28.8 mmol) of benzophenone was added thereto and stirred for 48 hours under refluxing. The reaction solution was poured into 100 ml of 2N hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted twice with 50 ml of hexane. It was combined with the previous organic layer and washed with a saturated sodium hydrogen carbonate aqueous solution, water and a saturated sodium chloride aqueous solution. The organic layer was dried on magnesium sulfate, and then the solvent was removed by distillation. Thereafter, the residue was purified by column chromatography to obtain 4.2 g of an orange solid matter. The yield was 56%. The product was identified by means of a 1H-NMR spectrum. The measurement results thereof are shown below.

Workup

  1. customobtained
  2. stirringstirred for 48 hours
  3. temperatureunder refluxing
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted twice with 50 ml of hexane
  6. washwashed with a saturated sodium hydrogen carbonate aqueous solution, water
  7. customThe organic layer was dried on magnesium sulfate
  8. customthe solvent was removed by distillation
  9. customThereafter, the residue was purified by column chromatography

Sources & evidence

ORD record
ord-12a4d7e620784b12ab35f83a046d116d
Source dataset
uspto-grants-2012_01
Patent number
US08101684B2

Reaction notes

Loading…