N-benzyl-7-bromo-1,2,3,4-tetrahydroquinoline → HCID 67115832、化合物

HRID 72628ノート

反応式

HRID 72628 の反応式
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15](Br)[CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[Br:24][C:25]1[CH:26]=[CH:27][C:28]([CH:33]([CH3:35])[CH3:34])=[C:29]([CH:32]=1)[CH:30]=[O:31]>C1COCC1>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH:30]([C:29]3[CH:32]=[C:25]([Br:24])[CH:26]=[CH:27][C:28]=3[CH:33]([CH3:35])[CH3:34])[OH:31])[CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 46894871N-benzyl-7-bromo-1,2,3,4-tetrahydroquinolineHCID 583408355-Bromo-2-isopropylbenzaldehydeHCID 178418339Butyllithium

生成物 1

HCID 67115832HCID 67115832、化合物収率 70.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 1-benzyl-7-bromo-1,2,3,4-tetrahydro-quinoline (2.50 g, 8.27 mmol) in THF (20 mL) was added 1.6 M n-butyl lithium in hexanes (5.14 mL, 8.27 mmol) at −78° C. The mixture was stirred for 45 min. then transferred to a stirred solution of 5-bromo-2-isopropylbenzaldehyde (1.87 g, 8.27 mmol) in THF (15 mL) at −78° C. After stirring for 30 min, the reaction was quenched by the addition of saturated aqueous solution of ammonium chloride, and the resulting mixture was extracted with ethyl acetate (3×30 mL). The organic layers were combined and washed with water (25 mL) and brine (25 mL), then dried over sodium sulfate, concentrated and purified using neutral alumina column chromatography to furnish (1-benzyl-1,2,3,4-tetrahydro-quinolin-7-yl)-(5-bromo-2-isopropyl-phenyl)-methanol (2.64 g).

後処理

  1. stirringAfter stirring for 30 min
  2. customthe reaction was quenched by the addition of saturated aqueous solution of ammonium chloride
  3. extractionthe resulting mixture was extracted with ethyl acetate (3×30 mL)
  4. washwashed with water (25 mL) and brine (25 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified

出典と根拠

ORDレコード
ord-90c156673cf14b9995c9d57f83fc6cca
出典データセット
uspto-grants-2014_09
特許番号
US08828951B2

反応ノート

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