Water → 5-Ethoxymethoxy-benzofuran

HRID 217206ノート

反応式

HRID 217206 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([OH:10])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].[CH2:13]([O:15][CH2:16]Cl)[CH3:14].O>CN(C=O)C>[CH2:13]([O:15][CH2:16][O:10][C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH:2]=[CH:3][C:4]=2[CH:9]=1)[CH3:14]

参加物

6

反応物 4

HCID 962WaterHCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydrideHCID 11651159Benzofuran-5-ol

生成物 1

HCID 592274505-Ethoxymethoxy-benzofuran

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of benzofuran-5-ol (2) (257 mg, 1.92 mmol) in DMF (3 mL), NaH (81 mg, 1.92 mmol, 57% dispersion in oil) was added at 0° C. The reaction mixture was warmed to room temperature and stirred 1 hour. Chloromethyl ethyl ether (214 μL, 2.30 mmol) was then added drop wise to 0° C. and the mixture was stirred at room temperature for additional 1 hour. Water (10 mL) was added and the reaction mixture was extracted with ethyl acetate (2×50 mL). The organic extracts were washed with water, brine, dried over Na2SO4, and concentrated in vacuo. Purification of the crude product by flash column chromatography using 10% ethyl acetate in hexane afforded compound (3) (273 mg) as a colourless oil.

後処理

  1. stirringthe mixture was stirred at room temperature for additional 1 hour
  2. extractionthe reaction mixture was extracted with ethyl acetate (2×50 mL)
  3. washThe organic extracts were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification of the crude product by flash column chromatography

出典と根拠

ORDレコード
ord-bcd7bfa677e64f72a143dd07740c793d
出典データセット
uspto-grants-2012_06
特許番号
US08193363B2

反応ノート

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