Hydrochloric Acid → 4,6-Di-tert-butyl-5-hydroxybenzofuran

HRID 1900526ノート

反応式

HRID 1900526 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][C:11]1[C:12]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:13][C:14]2[O:18][C:17](CCCCCCCC)=[CH:16][C:15]=2[C:27]=1[C:28]([CH3:31])([CH3:30])[CH3:29])(=O)C.O.Cl>O1CCCC1>[C:28]([C:27]1[C:15]2[CH:16]=[CH:17][O:18][C:14]=2[CH:13]=[C:12]([C:32]([CH3:35])([CH3:34])[CH3:33])[C:11]=1[OH:10])([CH3:31])([CH3:30])[CH3:29]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 184331765-Acetoxy-4,6-di-tert-butyl-2-octylbenzofuranHCID 21226445Aluminium lithium hydride

生成物 1

HCID 117707334,6-Di-tert-butyl-5-hydroxybenzofuran収率 132.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Lithium aluminum hydride (0.26 g) was suspended in tetrahydrofuran (50 ml) under a nitrogen atmosphere and a solution of 5-acetoxy-4,6-di-tert-butyl-2-octylbenzofuran (2.7 g) in tetrahydrofuran (20 ml) was added to the suspension under cooling with ice. After heating under reflux for 3 h, the mixture was cooled to room temperature and water was added dropwise. After adding 10% aqueous HCl (50 ml), the mixture was subjected to extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 4,6-di-tert-butyl-5-hydroxybenzofuran [2.2 g (yield, 92%)] as a colorless oil.

後処理

  1. temperatureunder cooling with ice
  2. temperatureAfter heating
  3. temperatureunder reflux for 3 h
  4. extractionthe mixture was subjected to extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane)

出典と根拠

ORDレコード
ord-0f2d93b2e1534167bb2d8d5d405e3898
出典データセット
uspto-grants-1996_11
特許番号
US05574178

反応ノート

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