Hydrochloric Acid → 3-tert-Butyl-1-ethylcyclopenta-1,3-diene

HRID 251305Notes

Reaction equation

HRID 251305 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[C:5]([C:9]1[CH2:13][CH2:12][C:11](=O)[CH:10]=1)([CH3:8])([CH3:7])[CH3:6].Cl>C(OCC)C>[CH2:1]([C:12]1[CH2:11][CH:10]=[C:9]([C:5]([CH3:8])([CH3:7])[CH3:6])[CH:13]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 119769972-Cyclopenten-1-one, 3-(1,1-dimethylethyl)-HCID 178418443HCID 178418443, compound

Product 1

HCID 206271323-tert-Butyl-1-ethylcyclopenta-1,3-dieneYield 104.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 300-ml three-necked flask equipped with a magnetic stirrer and a three-way cock in a nitrogen atmosphere was charged with 200 ml of dehydrated diethyl ether and 52 ml of a 3.0 M diethyl ether solution of ethylmagnesium bromide (154 mmol). In an ice water bath, 17.8 g (129 mmol) of 3-tert-butylcyclopentenone was added dropwise to the flack over a period of 1 hour. The mixture was stirred at room temperature for 20 hours, and the resultant reaction solution was poured into 100 ml of 2N hydrochloric acid. The organic phase was separated, and the aqueous phase was extracted with 50 ml of ether two times. The organic phases were combined and washed two times with a saturated aqueous sodium hydrogencarbonate solution, two times with water, and two times with a saturated salt solution. The product was dried over magnesium sulfate and the solvent was distilled off. The distillate was purified by column chromatography to give 20.2 g of a light yellow transparent liquid (GC purity: 75%). The yield was 78%. The compound was identified by 1H-NMR spectroscopy. The results are as follows.

Workup

  1. customA 300-ml three-necked flask equipped with a magnetic stirrer
  2. customthe resultant reaction solution
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with 50 ml of ether two times
  5. washwashed two times with a saturated aqueous sodium hydrogencarbonate solution, two times with water, and two times with a saturated salt solution
  6. dry with materialThe product was dried over magnesium sulfate
  7. distillationthe solvent was distilled off
  8. distillationThe distillate was purified by column chromatography

Sources & evidence

ORD record
ord-4f93fc654e7a41d488bbf3e2ce9a1a38
Source dataset
uspto-grants-2011_01
Patent number
US07863368B2

Reaction notes

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