Water → 4,6-Di-tert-butyl-2,2-diethyl-5-hydroxy-2,3-dihydrobenzofuran

HRID 1452363Notes

Reaction equation

HRID 1452363 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][C:11]1[C:12]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:13][C:14]2[O:18][C:17]([CH2:21][CH3:22])([CH2:19][CH3:20])[CH2:16][C:15]=2[C:23]=1[C:24]([CH3:27])([CH3:26])[CH3:25])(=O)C.O.[OH-].[Na+]>O1CCCC1>[C:24]([C:23]1[C:15]2[CH2:16][C:17]([CH2:19][CH3:20])([CH2:21][CH3:22])[O:18][C:14]=2[CH:13]=[C:12]([C:28]([CH3:29])([CH3:31])[CH3:30])[C:11]=1[OH:10])([CH3:25])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 110244525-Acetoxy-4,6-di-tert-butyl-2,2-diethyl-2,3-dihydrobenzofuranHCID 21226445Aluminium lithium hydride

Product 1

HCID 110987574,6-Di-tert-butyl-2,2-diethyl-5-hydroxy-2,3-dihydrobenzofuranYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (76 mg) was suspended in tetrahydrofuran (5 ml) under a nitrogen atmosphere. A solution of 5-acetoxy-4,6-di-tert-butyl-2,2-diethyl-2,3-dihydrobenzofuran (0.17 g, 0.5 mmol) in tetrahydrofuran (5 ml) was added dropwise to the suspension. After heating under reflux for 3 h, the reaction mixture was cooled to room temperature and water was added dropwise. After addition of 1N aqueous sodium hydroxide (5 ml), the mixture was subjected to extraction with diethyl ether. 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-2,2-diethyl-5-hydroxy-2,3-dihydrobenzofuran [130 mg (yield, 87%)] as a pale yellow oil.

Workup

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

Sources & evidence

ORD record
ord-9a59f57a4fca448b8eb8786fa519473a
Source dataset
uspto-grants-1997_02
Patent number
US05606089

Reaction notes

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