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

HRID 618721ノート

反応式

HRID 618721 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
10 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f36c733d391b4cd5a621cfbefcd38de5
出典データセット
uspto-grants-1999_09
特許番号
US05955495

反応ノート

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