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

HRID 892144ノート

反応式

HRID 892144 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-1f4301884b474332aafc444fae97cc31
出典データセット
uspto-grants-2006_02
特許番号
US07005440B1

反応ノート

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