Tetrahydrofuran → 6-Methoxy-7-(2-methoxyvinyl)quinoline

HRID 494967Notes

Reaction equation

HRID 494967 reaction equation
CC(C)([O-])C.[K+].[O:7]1[CH2:11]CC[CH2:8]1.[Cl-].COC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:35][O:36][C:37]1[CH:38]=[C:39]2[C:44](=[CH:45][C:46]=1[CH:47]=O)[N:43]=[CH:42][CH:41]=[CH:40]2>C(OCC)(=O)C>[CH3:35][O:36][C:37]1[CH:38]=[C:39]2[C:44](=[CH:45][C:46]=1[CH:47]=[CH:8][O:7][CH3:11])[N:43]=[CH:42][CH:41]=[CH:40]2

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxideHCID 576828846-Methoxyquinoline-7-carbaldehyde

Product 1

HCID 688560946-Methoxy-7-(2-methoxyvinyl)quinoline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

While cooling on ice, 0.82 g of potassium t-butoxide was added to 20 ml of a tetrahydrofuran suspension containing 2.50 g of (methoxymethyl)triphenylphosphonium chloride under nitrogen atmosphere. The obtained mixture was then stirred at the same temperature for 10 minutes. Thereafter, 3 ml of a tetrahydrofuran solution containing 545 mg of 6-methoxyquinoline-7-carbaldehyde was added to the reaction solution while cooling on ice, and the obtained mixture was then stirred at the same temperature for 15 minutes. Thereafter, the reaction solution was diluted with ethyl acetate, and then washed with water and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate), so as to obtain 1.41 g of 6-methoxy-7-(2-methoxyvinyl)quinoline containing triphenylphosphine oxide. This compound was used in the next reaction without further purification.

Workup

  1. additionwas added to the reaction solution
  2. temperaturewhile cooling on ice
  3. stirringthe obtained mixture was then stirred at the same temperature for 15 minutes
  4. washwashed with water
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under a reduced pressure
  7. customThe residue was purified by NH silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-79a6e2bb5a204a82ac5cc99f3a2d12fc
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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