1,3-Dibromopropane → HCID 53811470、化合物

HRID 342759ノート

反応式

HRID 342759 の反応式
[CH2:1]([C:3]1[C:4](=[O:17])[O:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([OH:13])[C:7]=2[CH2:14][CH2:15][CH3:16])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Br:24][CH2:25][CH2:26][CH2:27]Br>CN(C=O)C.C(OCC)(=O)C.[Cl-].[NH4+]>[Br:24][CH2:25][CH2:26][CH2:27][O:13][C:8]1[C:7]([CH2:14][CH2:15][CH3:16])=[C:6]2[C:11]([CH:12]=[C:3]([CH2:1][CH3:2])[C:4](=[O:17])[O:5]2)=[CH:10][CH:9]=1

参加物

7

反応物 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 53692562HCID 53692562、化合物

生成物 1

HCID 53811470HCID 53811470、化合物

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒HCID 25517Ammonium Chloride溶媒

実験手順

To a solution of 3-ethyl-7-hydroxy-8-propylcoumarin (37 mg, 0.1593 mmol) and potassium carbonate (44 mg, 0.3186 mmol) in 0.7 mL DMF was added 1,3-dibromopropane (161 mg, 0.08 mL). The mixture was stirred at ambient temperature for 2 hours and diluted with ethyl acetate and saturated (aqueous) ammonium chloride. After the layers were separated, the aqueous phase was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered, concentrated in vacuo, and the crude residue was purified by flash chromatography on silica gel (gradient elution: 5% then 10% then 20% ethyl acetate/hexane). This provided the title compound.

後処理

  1. customAfter the layers were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customthe crude residue was purified by flash chromatography on silica gel (
  8. washgradient elution

出典と根拠

ORDレコード
ord-f014b9b8e69d466eac58dc6096419682
出典データセット
uspto-grants-1999_01
特許番号
US05859051

反応ノート

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