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Water → 2-(3-(1-Hydroxyhexyl)benzyloxymethyl)quinoline

HRID 414845
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HRID 414845 반응식
[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.C1(C)C=CC(S(O[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([OH:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:25]=2)(=O)=O)=CC=1.C(N(CC)CC)C.O>C(Cl)Cl>[OH:36][CH:30]([C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[CH2:23][O:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 731962-QuinolinemethanolHCID 14349156HCID 14349156, 화합물

생성물 1

HCID 143491382-(3-(1-Hydroxyhexyl)benzyloxymethyl)quinoline수율 52%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

A mixture of 2-hydroxymethylquinoline (8 g, 0.05 mol) and 3-(1-hydroxyhexyl)benzyl p-toluenesulfonate (18.2 g, 0.05 mol; prepared as in Example 17) in methylene chloride (200 ml) containing triethylamine (15 ml) was stirred at 0° C. for 4 hours, and then allowed to warm up to room temperature. This mixture was stirred for two more hours at this temperature, and then poured into water. The organic layer was separated and washed with dilute sodium hydroxide solution, water and brine. After drying the organics, all volatiles were removed to obtain the crude product as a yellowish brown liquid. This was purified by chromatography on silica gel using 15% ethyl acetate in hexanes to get the pure product as a clear, light yellow liquid (9 g, 52% yield).

후처리

  1. temperatureto warm up to room temperature
  2. stirringThis mixture was stirred for two more hours at this temperature
  3. customThe organic layer was separated
  4. washwashed with dilute sodium hydroxide solution, water and brine
  5. customAfter drying the organics, all volatiles
  6. customwere removed
  7. customto obtain the crude product as a yellowish brown liquid
  8. customThis was purified by chromatography on silica gel using 15% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-dc306c2b8cba4440b81679cf03bb421f
출처 데이터셋
uspto-grants-1988_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04794188

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