Water → HCID 18433151, compound

HRID 1376976Notes

Reaction equation

HRID 1376976 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 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (0.08 g) was suspended tn 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-a2e3b99b95404f1e993fbabb1e3ebe0b
Source dataset
uspto-grants-1997_09
Patent number
US05663373

Reaction notes

Loading…