Hydrochloric Acid → HCID 86619896, compound

HRID 1361558Notes

Reaction equation

HRID 1361558 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].[CH3:12]O.N1CC[CH2:16][CH2:15]1.Cl>CC(C)=O>[C:8]([C:5]1[CH:6]=[C:7]([CH2:15][CH3:16])[C:3](=[C:1]([CH3:12])[CH3:2])[CH:4]=1)([CH3:10])([CH3:9])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 31268PyrrolidineHCID 206271323-tert-Butyl-1-ethylcyclopenta-1,3-diene

Product 1

HCID 86619896HCID 86619896, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a 100 ml three-neck flask equipped with a magnetic stirrer chip and a three-way cock, 3.12 g (20.8 mmol) of 1-ethyl-3-tert-butylcyclopentadiene, 30 ml of methanol, 19 ml of acetone and 20 ml of pyrrolidine were charged under a nitrogen atmosphere, and stirred at room temperature for 6 days. The reaction solution was poured into 200 ml of 2N hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted three times with 100 ml of ether. The obtained organic layers were combined, washed once with a saturated aqueous solution of sodium hydrogencarbonate, twice with water, and once with saturated brine, dried over magnesium sulfate, and purified by column chromatography to obtain 2.91 g of a orange solution. The yield was 74%. Identification was done by 1H-NMR spectrum. The measurement results are shown as follows.

Workup

  1. customTo a 100 ml three-neck flask equipped with a magnetic stirrer chip
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted three times with 100 ml of ether
  4. washwashed once with a saturated aqueous solution of sodium hydrogencarbonate, twice with water
  5. dry with materialonce with saturated brine, dried over magnesium sulfate
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-03208d4130ea41cbb42a5d9fea0d941b
Source dataset
uspto-grants-2011_02
Patent number
US07879960B2

Reaction notes

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