Methyltriphenylphosphonium chloride → HCID 67317831, compound

HRID 1013738Notes

Reaction equation

HRID 1013738 reaction equation
[Cl-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[CH3:27][O:28][C:29]1[CH:38]=[C:37]2[C:32]([C:33]([C:39]([C:41]3[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][CH:42]=3)=O)=[CH:34][CH:35]=[N:36]2)=[CH:31][CH:30]=1>C1COCC1>[CH3:27][O:28][C:29]1[CH:38]=[C:37]2[C:32]([C:33]([C:39]([C:41]3[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][CH:42]=3)=[CH2:2])=[CH:34][CH:35]=[N:36]2)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 9879809Methyltriphenylphosphonium chlorideHCID 67317464HCID 67317464, compoundHCID 178418339Butyllithium

Product 1

HCID 67317831HCID 67317831, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of methyltriphenylphosphonium chloride (0.54 g, 1.7 mmol) in THF (10 mL) at −78° C. was added n-butyllithium, 2.5 M in hexanes (0.80 ml, 2.0 mmol). After 20 min, a mixture of (7-methoxyquinolin-4-yl)(4-nitrophenyl)methanone (0.177 g, 0.57 mmol) in THF (5 mL) was slowly added. After 10 min, the mixture was allowed to warm to RT. The reaction was quenched with saturated aqueous NH4Cl. The mixture was diluted with EtOAc and washed with water and brine. After drying the organic fraction with Na2SO4, the solvent was removed in vacuo and the residue purified by silica gel chromatography using 40-100% hexanes:EtOAc to afford 7-methoxy-4-(1-(4-nitrophenyl)vinyl)quinoline as a yellow foam. MS: M+H+=307.1.

Workup

  1. additionwas slowly added
  2. waitAfter 10 min
  3. customThe reaction was quenched with saturated aqueous NH4Cl
  4. additionThe mixture was diluted with EtOAc
  5. washwashed with water and brine
  6. dry with materialAfter drying the organic fraction with Na2SO4
  7. customthe solvent was removed in vacuo
  8. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-d87dd181061741268c93c19e6aeb6044
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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