Hydrochloric Acid → HCID 86619564, compound

HRID 1050675Notes

Reaction equation

HRID 1050675 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(=O)=O.CO.CCCCCC.C([Li])CCC.CN1CCN(C)C1=O.[C:36]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)(=O)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.Cl>C1COCC1>[C:8]([C:5]1[CH:4]=[C:3]([CH2:1][CH3:2])[C:7](=[C:36]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:6]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 3102BenzophenoneHCID 66611,3-Dimethyl-2-imidazolidinoneHCID 206271323-tert-Butyl-1-ethylcyclopenta-1,3-dieneHCID 21973728Carbon dioxide methanolHCID 178418244HCID 178418244, compound

Product 1

HCID 86619564HCID 86619564, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, a 300 ml three-neck flask equipped with a magnetic stirrer chip and a three-way cock was charged with 5.11 g (23.9 mmol) of 1-ethyl-3-tert-butylcyclopentadiene (75% GC purity) and 150 ml of THF. In the dry ice/methanol bath, 16 ml (25.2 mmol) of 1.56M n-butyllithium hexane solution was gradually added dropwise and the mixture was then stirred at room temperature for 20 hours. Then, 3.1 ml (28.8 mmol) of 1,3-dimethyl-2-imidazolidinone and 5.3 g (28.8 mmol) of benzophenone were sequentially added to the reaction solution obtained, and the solution was stirred for 48 hours under reflux. 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 organic layers obtained were combined with the organic layer previously obtained. The liquid was washed with a saturated aqueous solution of sodium hydrogencarbonate, water, and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography to obtain 4.2 g of an orange solid. The yield was 56%. Identification was done by 1H-NMR spectrum. The measurement results are shown as follows.

Workup

  1. customUnder a nitrogen atmosphere, a 300 ml three-neck flask equipped with a magnetic stirrer chip
  2. customobtained
  3. stirringthe solution was stirred for 48 hours
  4. temperatureunder reflux
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was subjected to extraction with 50 ml of hexane twice
  7. customThe organic layers obtained
  8. custompreviously obtained
  9. washThe liquid was washed with a saturated aqueous solution of sodium hydrogencarbonate, water
  10. dry with materiala saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
  11. distillationThe solvent was distilled off
  12. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-642df69048b546a8a8cc8f432067b74d
Source dataset
uspto-grants-2016_07
Patent number
US09382356B2

Reaction notes

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