Thionyl Chloride → 2-Chloromethylbenzofuran

HRID 1030267

반응식

HRID 1030267 반응식
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

참가 물질

6

반응물 2

HCID 24386Thionyl ChlorideHCID 27762631-Benzofuran-2-Ylmethanol

생성물 1

HCID 1843482-Chloromethylbenzofuran수율 70.8%

시약·촉매·용매 3

HCID 1049Pyridine촉매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c012e877cce043cf851bd73ad11690a6
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05104892

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