Hydrochloric Acid → HCID 18798450, compound

HRID 1361566Notes

Reaction equation

HRID 1361566 reaction equation
O1C[CH2:4][CH2:3][CH2:2]1.C([Mg]Br)CC.[C:11]([C:15]1[CH2:19][CH2:18][C:17](=O)[CH:16]=1)([CH3:14])([CH3:13])[CH3:12].Cl>C(OCC)C>[CH2:2]([C:18]1[CH2:17][CH:16]=[C:15]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:19]=1)[CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 119769972-Cyclopenten-1-one, 3-(1,1-dimethylethyl)-HCID 178455851HCID 178455851, compound

Product 1

HCID 18798450HCID 18798450, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 300 ml three-neck flask equipped with a magnetic stirrer chip and a three-way cock, 120 ml of dehydrated diethyl ether and 89 ml (178 mmol) of tetrahydrofuran solution of 2.0M n-propyl magnesium bromide were charged under a nitrogen atmosphere. In the ice bath, 20.6 g (149 mmol) of 3-tert-butylcyclopentenone was added dropwise over 1 hour. The resultant solution was stirred at room temperature for 20 hours, and then 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 ether. The obtained organic layers were combined, washed twice with a saturated aqueous solution of sodium hydrogencarbonate, twice with water and twice with saturated brine, and dried over magnesium sulfate and the solvent was distilled off. Thereafter, the resulting product was purified by column chromatography to obtain 16.8 g (GC purity 82%) of a pale yellowy transparent liquid. The yield was 57%. Identification was done by 1H-NMR spectrum. The measurement results are shown as follows.

Workup

  1. customTo a 300 ml three-neck flask equipped with a magnetic stirrer chip
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted twice with 50 ml of ether
  4. washwashed twice with a saturated aqueous solution of sodium hydrogencarbonate, twice with water and twice with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThereafter, the resulting product was purified by column chromatography
  8. customto obtain 16.8 g (GC purity 82%) of a pale yellowy transparent liquid
  9. customThe measurement results

Sources & evidence

ORD record
ord-b0f7d0df829542369e33c59a0aed62df
Source dataset
uspto-grants-2011_02
Patent number
US07879960B2

Reaction notes

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