Water → 2,2-Diisoamyl-4,6-di-tert-butyl-5-hydroxy-2,3-dihydrobenzofuran

HRID 1900517ノート

反応式

HRID 1900517 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][C:11]1[C:12]([C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:13][C:14]2[O:18][C:17]([CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:16][C:15]=2[C:29]=1[C:30]([CH3:33])([CH3:32])[CH3:31])(=O)C.O.[Cl-].[NH4+]>O1CCCC1>[CH2:24]([C:17]1([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:16][C:15]2[C:29]([C:30]([CH3:33])([CH3:32])[CH3:31])=[C:11]([OH:10])[C:12]([C:34]([CH3:35])([CH3:36])[CH3:37])=[CH:13][C:14]=2[O:18]1)[CH2:25][CH:26]([CH3:28])[CH3:27]

参加物

6

反応物 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 111128205-Acetoxy-2,2-diisoamyl-4,6-di-tert-butyl-2,3-dihydrobenzofuranHCID 21226445Aluminium lithium hydride

生成物 1

HCID 110473792,2-Diisoamyl-4,6-di-tert-butyl-5-hydroxy-2,3-dihydrobenzofuran収率 57.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Lithium aluminum hydride (1.90 g) was suspended in tetrahydrofuran (200 ml) under a nitrogen atmosphere. A solution of 5-acetoxy-2,2-diisoamyl-4,6-di-tert-butyl-2,3-dihydrobenzofuran (17.4 g) in tetrahydrofuran (60 ml) was added dropwise to the suspension under cooling with ice. After heating under reflux overnight, the mixture was cooled to room temperature and water and a saturated aqueous solution of ammonium chloride were added in that order. The resulting insolubles were filtered off on Celite. The filtrate was subjected to extraction with diethyl ether, washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was distilled off. The residue was purified by silica gel chromatography (n-hexane) to afford 2,2-diisoamyl-4,6-di-tert-butyl-5-hydroxy-2,3-dihydrobenzofuran [9.0 g (yield, 57%)] as a colorless oil.

後処理

  1. temperatureunder cooling with ice
  2. temperatureAfter heating
  3. temperatureunder reflux overnight
  4. filtrationThe resulting insolubles were filtered off on Celite
  5. extractionThe filtrate was subjected to extraction with diethyl ether
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off
  9. customThe residue was purified by silica gel chromatography (n-hexane)

出典と根拠

ORDレコード
ord-a5e8d768a7b548b89e27849a0b5fd93b
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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