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

HRID 1452374Notes

Reaction equation

HRID 1452374 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-662f34aca7154a6ea1bbb4871107875e
Source dataset
uspto-grants-1997_02
Patent number
US05606089

Reaction notes

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