Thionyl Chloride → 2-Chloromethylbenzofuran

HRID 1030267ノート

反応式

HRID 1030267 の反応式
S(Cl)([Cl:3])=O.[O:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH:7]=[C:6]1[CH2:14]O>N1C=CC=CC=1.C(Cl)Cl.O>[Cl:3][CH2:14][C:6]1[O:5][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH:7]=1

参加物

6

反応物 2

HCID 24386Thionyl ChlorideHCID 27762631-Benzofuran-2-Ylmethanol

生成物 1

HCID 1843482-Chloromethylbenzofuran収率 70.8%

試薬・触媒・溶媒 3

HCID 1049Pyridine触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

Thionyl chloride (5.14 mL, 70.46 mmol) was added dropwise to a solution of benzofuran-2-methanol (3.58 g, 23.48 mmol) and pyridine (10 drops) in methylene chloride (60 mL). Stirring was continued at room temperature for 18 hours. The mixture was carefully diluted with water and extracted with methylene chloride. The organic extracts were washed with aqueous sodium bicarbonate, dried (MgSO4) and concentrated to afford crude product which was purified by flash column chromatography (10% EtOAc/hexanes) to afford 2.77 g (69%) of pure product as a yellow oil.

後処理

  1. extractionextracted with methylene chloride
  2. washThe organic extracts were washed with aqueous sodium bicarbonate
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto afford crude product which
  6. customwas purified by flash column chromatography (10% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-c012e877cce043cf851bd73ad11690a6
出典データセット
uspto-grants-1992_04
特許番号
US05104892

反応ノート

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