Water → 1-Methoxybicyclo[2.2.2]oct-5-en-2-one

HRID 451791Notes

Reaction equation

HRID 451791 reaction equation
Cl[C:2]1(C#N)[CH2:7][CH:6]2[CH2:8][CH2:9][C:3]1([O:10][CH3:11])[CH:4]=[CH:5]2.[OH2:14]>C(O)C>[CH3:11][O:10][C:3]12[CH2:9][CH2:8][CH:6]([CH:5]=[CH:4]1)[CH2:7][C:2]2=[O:14]

Participants

4

Reactant 2

HCID 962WaterHCID 126140392-Chloro-1-methoxybicyclo[2.2.2]oct-5-ene-2-carbonitrile

Product 1

HCID 3772231-Methoxybicyclo[2.2.2]oct-5-en-2-oneYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-chloro-1-methoxybicyclo[2.2.2]oct-5-ene-2-carbonitrile (14.0 g, 71 mmol) and Na2S.9H2O (34.0 g, 142 mmol) in ethanol (175 mL) was heated under reflux for 14 h. The solution was poured into H2O and extracted three times with ether. The combined extracts were washed with saturated aqueous NH4Cl solution, H2O, and brine. The organic layer was dried over Na2SO4, concentrated to the residue. The crude product was purified by column chromatography to afford 1-methoxybicyclo[2.2.2]oct-5-en-2-one (5.7 g, 57%). 1H NMR (CDCl3, 400 MHz) δ 6.46 (dd, 1H), 6.22 (d, 1H), 3.50 (s, 3H), 2.94 (m, 1H), 2.11 (m, 2H), 1.53-1.92 (m, 4H).

Workup

  1. temperatureunder reflux for 14 h
  2. extractionextracted three times with ether
  3. washThe combined extracts were washed with saturated aqueous NH4Cl solution, H2O, and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated to the residue
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-d6615686862a47b4a7091882cef04e8a
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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