Potassium Iodide → 6-Ethoxy-5-[3-(tetrahydro-pyran-2-yloxy)-propoxy]-indan-1-one

HRID 1714453ノート

反応式

HRID 1714453 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[OH:11])[C:7](=[O:12])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][CH2:21][CH2:22][O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1.[I-].[K+].[CH2:32](Br)[CH3:33]>CN(C=O)C.C(OCC)(=O)C>[CH2:32]([O:11][C:10]1[CH:9]=[C:8]2[C:4]([CH2:5][CH2:6][C:7]2=[O:12])=[CH:3][C:2]=1[O:1][CH2:20][CH2:21][CH2:22][O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1)[CH3:33]

参加物

8

反応物 5

HCID 4875Potassium IodideHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 2549542-(3-Chloropropoxy)oxane2 回HCID 115934875,6-Dihydroxy-2,3-dihydro-1H-inden-1-one2 回

生成物 1

HCID 184458066-Ethoxy-5-[3-(tetrahydro-pyran-2-yloxy)-propoxy]-indan-1-one

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

A mixture of 5,6-dihydroxy-indan-1-one (Intermediate O) (1.80 g, 0.01098 mole), potassium carbonate (3.80 g, 0.02744 mol), 2-(3-chloro-propoxy)-tetrahydro-pyran (Compound 18a) (1.37 g, 0.00769 mol) and potassium iodide (1.28 g, 0.00769 mol) in DMF (20 mL) was stirred at 60° C. for 4 hours. To this mixture was then added ethyl bromide (1.64 mL, 0.02196 mol) and continued to heat for further 4 h. The reaction mixture was then diluted with ethyl acetate, washed with water and dried over MgSO4. The solvent was removed in vacuo and the title compound was purified by silica gel column chromatography using 3:1 Hexanes:ethyl acetate as the eluent. MS m/z 334.2 (M+H)+;

後処理

  1. temperatureto heat for further 4 h
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed in vacuo
  5. customthe title compound was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-5eb72317b1d04f09b06944c027c945c4
出典データセット
uspto-grants-2010_09
特許番号
US07795440B2

反応ノート

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