Water → 2-[3-(Quinolin-2-ylmethoxy)-benzyloxy]-benzaldehyde

HRID 892180노트

반응식

HRID 892180 반응식
Cl.Cl[CH2:3][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[O:7][CH2:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.[CH:22](=[O:30])[C:23]1[C:24](=[CH:26][CH:27]=[CH:28][CH:29]=1)[OH:25].C([O-])([O-])=O.[K+].[K+].O>CC(C)=O>[N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[CH:18][C:9]=1[CH2:8][O:7][C:6]1[CH:5]=[C:4]([CH:21]=[CH:20][CH:19]=1)[CH2:3][O:25][C:24]1[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=1[CH:22]=[O:30]

참가 물질

6

반응물 4

HCID 962WaterHCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 145017072-(3-Chloromethylphenoxymethyl)quinoline hydrochloride

생성물 1

HCID 222412772-[3-(Quinolin-2-ylmethoxy)-benzyloxy]-benzaldehyde

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

2-(3-Chloromethyl-phenoxymethyl)-quinoline (371 mg, 1.3 mmol, example 49) and salicylaldehyde (133 μL, 1.25 mmol) are dissolved in acetone (10 mL). K2CO3 (525 mg, 3.75 mmol) is added and the contents are heated to reflux for 16 hrs. The reaction is cooled to r.t., poured into water (100 mL) and extracted with ethyl ether (3×50 mL). The ether layers are combined and washed with Brine (3×75 mL) and dried over MgSO4. The crude material is preadsorbed onto silica gel and purified by flash chromatography (silica, 20 to 25% ethyl acetate in hexanes) to give the title compound. MS (ion spray) 370 (M+H)+.

후처리

  1. temperaturethe contents are heated
  2. temperatureto reflux for 16 hrs
  3. extractionextracted with ethyl ether (3×50 mL)
  4. washwashed with Brine (3×75 mL)
  5. dry with materialdried over MgSO4
  6. custompurified by flash chromatography (silica, 20 to 25% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-ac61e949e58740768d1dd9b8ef9f2a63
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07005440B1

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