2,6-Dimethylbenzaldehyde → HCID 66653558, 화합물

HRID 571781노트

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HRID 571781 반응식
[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

참가 물질

5

반응물 3

HCID 5838412,6-DimethylbenzaldehydeHCID 580978794-Benzyl-2-(4-bromo-phenyl)-morpholineHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 66653558HCID 66653558, 화합물수율 65.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-00abeba8676141739e8e49d1e48eab63
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029371B2

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