Hydrochloric Acid → 1-(4-Fluoro-2-methyl-benzofuran-7-yl)-propan-1-ol

HRID 618721노트

반응식

HRID 618721 반응식
Br[C:2]1[C:10]2[O:9][C:8]([CH3:11])=[CH:7][C:6]=2[C:5]([F:12])=[CH:4][CH:3]=1.[CH:13](=[O:16])[CH2:14][CH3:15].Cl>O1CCCC1>[F:12][C:5]1[C:6]2[CH:7]=[C:8]([CH3:11])[O:9][C:10]=2[C:2]([CH:13]([OH:16])[CH2:14][CH3:15])=[CH:3][CH:4]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 527PropanalHCID 218483217-Bromo-4-fluoro-2-methylbenzofuran

생성물 1

HCID 218482911-(4-Fluoro-2-methyl-benzofuran-7-yl)-propan-1-ol수율 68.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
10 °C

실험 절차

A solution of 5.75 g (25.1 mmol) of 7-bromo-4-fluoro-2-methylbenzofuran in 90 ml of tetrahydrofuran was added dropwise to a suspension of 0.625 g (27.5 mmol) of Mg in 100 ml of boiling tetrahydrofuran and the mixture was stirred at reflux for 2.5 hours. Subsequently, it was cooled to 10° C., 2.75 ml (37.5 mmol) of propionaldehyde were added dropwise thereto and the mixture was stirred for 30 minutes. The mixture was poured into 200 ml of 1N hydrochloric acid and extracted three times with 150 ml of dichloromethane. After drying over sodium sulfate concentration was carried out in a vacuum. The crude product obtained was purified by column chromatography on silica gel (dichloro-methane/hexane 4:1). 3.6 g (55%) of 1-(4-fluoro-2-methyl-benzofuran-7-yl)-propan-1-ol were obtained as a pale yellow oil.

후처리

  1. temperatureat reflux for 2.5 hours
  2. stirringthe mixture was stirred for 30 minutes
  3. extractionextracted three times with 150 ml of dichloromethane
  4. dry with materialAfter drying over sodium sulfate concentration
  5. customThe crude product obtained
  6. customwas purified by column chromatography on silica gel (dichloro-methane/hexane 4:1)

출처 및 근거

ORD 기록
ord-f36c733d391b4cd5a621cfbefcd38de5
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05955495

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