3-[(2-Methoxyethoxy)methoxy]benzaldehyde → 1-(2-Methoxyethoxy)-methoxy-3-(2-quinolin-2-yl-vinyl)-benzene

HRID 892144Notes

Reaction equation

HRID 892144 reaction equation
[Cl-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)C=CC=CC=1.C([Li])CCC.[CH3:37][O:38][CH2:39][CH2:40][O:41][CH2:42][O:43][C:44]1[CH:45]=[C:46]([CH:49]=[CH:50][CH:51]=1)[CH:47]=O>C1COCC1>[CH3:37][O:38][CH2:39][CH2:40][O:41][CH2:42][O:43][C:44]1[CH:51]=[CH:50][CH:49]=[C:46]([CH:47]=[CH:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH:45]=1

Participants

5

Reactant 3

HCID 157551753-[(2-Methoxyethoxy)methoxy]benzaldehydeHCID 22241267Triphenyl[(quinolin-2-yl)methyl]phosphanium chlorideHCID 178418339Butyllithium

Product 1

HCID 544075821-(2-Methoxyethoxy)-methoxy-3-(2-quinolin-2-yl-vinyl)-benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (−78° C.) suspension of triphenyl-(quinolin-2-yl-methyl)-phosphonium chloride (1.76 g, 4 mmol, example 17) in THF (24 mL) is added, dropwise, n-butyl lithium solution (1.7 mL, 2.5 M in hexanes). The resulting mixture is stirred for 30 min. then a solution of 3-[(2-methoxyethoxy)-methoxy]-benzaldehyde (756 mg, 3.6 mmol, example 8a) in THF (3 mL) is added. This mixture is stirred for 30 min then the cold bath removed and stirring continued for 2 h. The reaction mixture is then diluted with ethyl acetate, washed with sat. ammonium acetate solution and brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (silica, 40% ethyl acetate in hexanes) to give the title compound as an oil. MS (ESI) 336 (M+H)+.

Workup

  1. temperatureTo a cooled
  2. additionis added
  3. stirringThis mixture is stirred for 30 min
  4. customthe cold bath removed
  5. stirringstirring
  6. waitcontinued for 2 h
  7. additionThe reaction mixture is then diluted with ethyl acetate
  8. washwashed with sat. ammonium acetate solution and brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated
  11. customThe residue is purified by flash chromatography (silica, 40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-1f4301884b474332aafc444fae97cc31
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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