Water → HCID 18433151, compound

HRID 1900503Notes

Reaction equation

HRID 1900503 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][C:11]1[C:12]([C:29]([CH3:32])([CH3:31])[CH3:30])=[C:13]([CH2:26][CH2:27][CH3:28])[C:14]2[O:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]=2[C:21]=1[C:22]([CH3:25])([CH3:24])[CH3:23])(=O)C.O>O1CCCC1>[OH:10][C:11]1[C:12]([C:29]([CH3:30])([CH3:32])[CH3:31])=[C:13]([CH2:26][CH2:27][CH3:28])[C:14]2[O:18][C:17]([CH3:19])([CH3:20])[CH2:16][C:15]=2[C:21]=1[C:22]([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 962WaterHCID 18433185HCID 18433185, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18433151HCID 18433151, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (0.08 g) was suspended in tetrahydrofuran (5 ml) under a nitrogen atmosphere. A solution of 5-acetoxy-4,6-di-tert-butyl-2,2-dimethyl-7-propyl-2,3-dihydrobenzofuran (0.60 g) in tetrahydrofuran (5 ml) was added dropwise to the suspension and the mixture was refluxed for 4 h. After cooling the reaction mixture to room temperature, water was added dropwise to quench the excess lithium aluminum hydride. Thereafter 1N aqueous sodium hydroxide (5 ml) was added and the mixture was subjected to extraction with diethyl ether, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (5% ethyl acetate in n-hexane) to afford 5-hydroxy-4,6-di-tert-butyl-2,2-dimethyl-7-propyl-2,3-dihydrobenzofuran [0.17 g (yield, 32%)] as a pale yellow solid.

Workup

  1. temperaturethe mixture was refluxed for 4 h
  2. customto quench the excess lithium aluminum hydride
  3. additionThereafter 1N aqueous sodium hydroxide (5 ml) was added
  4. extractionthe mixture was subjected to extraction with diethyl ether
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe concentrate was purified by silica gel chromatography (5% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-cff41c0e091d444ebd37c48aa8a11b28
Source dataset
uspto-grants-1996_11
Patent number
US05574178

Reaction notes

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