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

HRID 414845
ノート
印刷プレビュー

反応式

HRID 414845 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 731962-QuinolinemethanolHCID 14349156HCID 14349156、化合物

生成物 1

HCID 143491382-(3-(1-Hydroxyhexyl)benzyloxymethyl)quinoline収率 52%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-dc306c2b8cba4440b81679cf03bb421f
出典データセット
uspto-grants-1988_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04794188

反応ノート

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