4-Methoxybenzyl alcohol → 2-Chloro-4-(4-methoxybenzyloxy)quinoline

HRID 430067

반응식

HRID 430067 반응식
[Cl:1][C:2]1[CH:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[H-].[Na+].C1OCCOCCOCCOCCOC1.[CH3:30][O:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][OH:37])=[CH:34][CH:33]=1>C1COCC1>[Cl:1][C:2]1[CH:11]=[C:10]([O:37][CH2:36][C:35]2[CH:38]=[CH:39][C:32]([O:31][CH3:30])=[CH:33][CH:34]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

참가 물질

6

반응물 4

HCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 6075032,4-Dichloroquinoline

생성물 1

HCID 183536712-Chloro-4-(4-methoxybenzyloxy)quinoline수율 39%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2,4-Dichloroquinoline (4.48 g, 25 mmol) was dissolved in dry THF (100 ml) and treated with sodium hydride (60% dispersion in oil, 5.62 g 25 mmol) under an argon atmosphere portion-wise over a period of 20 min. After a further 30 min the reaction mixture was treated with 15-crown-5 (5.62 g, 25 mmol) followed by 4-methoxybenzyl alcohol (3.44 g, 23 mmol). The reaction was stirred at room temperature overnight. The reaction mixture was then evaporated to low volume, and partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and evaporated. Chromatography on Kieselgel 60 eluting with 10% ethyl acetate in hexane afforded the title compound as a white solid (2.67 g, 39%); δH (CDCl3) 5.20 (2H, s), 6.83 (1H, s), 6.97 and 7.43 (4H, 2×d, J=8.6 Hz), 7.49 (1H, t, J=8.1 Hz), 7.70 (1H, t, J=8.2 Hz), 7.94 (1H, d, J=8.3 Hz), 8.17 (1H, d, J=8.2 Hz); MS (ES+) 300 (MH+, 10%). 121 (100).

후처리

  1. customThe reaction mixture was then evaporated to low volume
  2. custompartitioned between water and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

출처 및 근거

ORD 기록
ord-361fc9a83b404743950446eea26116e0
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06320051B1

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