2,6-Dimethylbenzaldehyde → HCID 66653558、化合物

HRID 588234ノート

反応式

HRID 588234 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])(C)(C)C.[CH3:26][C:27]1[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[C:28]=1[CH:29]=[O:30]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([CH:29]([C:28]3[C:31]([CH3:35])=[CH:32][CH:33]=[CH:34][C:27]=3[CH3:26])[OH:30])=[CH:16][CH:15]=2)[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 5838412,6-DimethylbenzaldehydeHCID 580978794-Benzyl-2-(4-bromo-phenyl)-morpholineHCID 178418306HCID 178418306、化合物

生成物 1

HCID 66653558HCID 66653558、化合物収率 65.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 4-benzyl-2-(4-bromo-phenyl)-morpholine (2.1 g, 6.3 mmol) in THF (30 mL), at −78° C., was added dropwise t-butyl lithium (7.9 mL; 1.6 mol/l in heptanes; 12.6 mmol). The mixture was stirred for 20 min. at −78° C., and subsequently 2,6-dimethylbenzaldehyde (1 g, 7.6 mmol) was added. The mixture was allowed to warm to RT and stirred overnight. The resulting mixture was partitioned between water and EtOAc. The layers were separated. The organic layer was washed with water, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (EtOAc:heptanes 1:1) to afford [4-(4-benzyl-morpholin-2-yl)-phenyl]-(2,6-dimethyl-phenyl)-methanol (1.6 g), which was used as such in the next step.

後処理

  1. temperatureto warm to RT
  2. stirringstirred overnight
  3. customThe resulting mixture was partitioned between water and EtOAc
  4. customThe layers were separated
  5. washThe organic layer was washed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (EtOAc:heptanes 1:1)

出典と根拠

ORDレコード
ord-a44f2e1d927f460eac1bef8304ed91ea
出典データセット
uspto-grants-2016_01
特許番号
US09227960B2

反応ノート

読み込み中…