Methyl iodide → Ethyl 2-methoxy-6-methyl-4-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoate

HRID 892189노트

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HRID 892189 반응식
[OH:1][C:2]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)[CH:16]=2)[CH:10]=[C:9]([CH3:33])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[H-].[Na+].I[CH3:37]>CN(C=O)C>[CH3:37][O:1][C:2]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)[CH:16]=2)[CH:10]=[C:9]([CH3:33])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

참가 물질

5

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HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22241340Ethyl 2-hydroxy-6-methyl-4-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoate

생성물 1

HCID 22241415Ethyl 2-methoxy-6-methyl-4-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

To a solution of ethyl 2-hydroxy-6-methyl-4-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoate (150 mg, 0.34 mmol, example 65) in DMF (5 mL) is added sodium hydride (60%, 14 mg, 0.34 mmol) and the reaction is stirred 20 min. Iodomethane (0.03 mL, 0.5 mmol) is added and the reaction is heated at 50° C. for 7 h. The reaction is concentrated in vacuo and the residue is partioned between dichloromethane and aqueous ammonium chloride. The water layer is back-extracted with dichloromethane, the organic phases are combined, dried over magnesium sulfate, filtered and concentrated to yield crude product. The residue is purified by column chromatography (silica, 10 to 20% ethyl acetate in hexanes to provide the title compound; MS (ESI) 458 (M+H)+.

후처리

  1. concentrationThe reaction is concentrated in vacuo
  2. extractionThe water layer is back-extracted with dichloromethane
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield crude product
  7. customThe residue is purified by column chromatography (silica, 10 to 20% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-9249f797e23c49c3acdbf5c5471a2da0
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07005440B1

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