Hydrochloric Acid → HCID 86619564, compound

HRID 1361557Notes

Reaction equation

HRID 1361557 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.[C:23]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl>CN(C)P(=O)(N(C)C)N(C)C.C1COCC1>[C:8]([C:5]1[CH:4]=[C:3]([CH2:1][CH3:2])[C:7](=[C:23]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

7

Reactant 4

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

Product 1

HCID 86619564HCID 86619564, compoundYield 53.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

To a 200 ml three-neck flask equipped with a magnetic stirrer chip and a three-way cock, 3.16 g (21.2 mmom) of 1-ethyl-3-tert-butyl-cyclopentadiene and 100 ml of THF were charged under a nitrogen atmosphere. In the ice/methanol bath, 14 ml (22 mmol) of 1.58M n-butyllithium hexane solution was added dropwise over 45 minutes and stirred for 4 hours. Thereto, 8 ml of hexamethylphosphoric triamide, subsequently 5.85 g (32.1 mmol) of benzophenone were charged, and the solution was stirred for 27 hours at room temperature. The reaction solution was poured into 400 ml of 2N hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted with 150 ml of ether. The obtained organic layers were combined, washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated aqueous solution of sodium chloride, and dried over magnesium sulfate and the solvent was distilled off, and purified by column chromatography to obtain 3.51 g of an orange solid. The yield was 53%. Identification was done by 1H-NMR spectrum. The measurement results are shown as follows.

Workup

  1. customTo a 200 ml three-neck flask equipped with a magnetic stirrer chip
  2. stirringthe solution was stirred for 27 hours at room temperature
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with 150 ml of ether
  5. washwashed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. distillationthe solvent was distilled off
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-3b142c3c5fed4b2e913d85e33d023934
Source dataset
uspto-grants-2011_02
Patent number
US07879960B2

Reaction notes

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