Sodium hydride → (3-((Tert-butyldimethylsilyloxy)methyl)phenyl)methanol

HRID 1351092Notes

Reaction equation

HRID 1351092 reaction equation
[C:1]1([CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.[H-].[Na+].[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>O1CCCC1>[Si:13]([O:8][CH2:7][C:3]1[CH:2]=[C:1]([CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 693741,3-Benzenedimethanol

Product 1

HCID 10658493(3-((Tert-butyldimethylsilyloxy)methyl)phenyl)methanolYield 28.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,3-benzenedimethanol (1 g) in tetrahydrofuran (10 mL) was added sodium hydride (60%, 318 mg) under ice-cooling, and the mixture was stirred for 30 minutes. To the reaction mixture was added tert-butyldimethylsilyl chloride (1.09 g), and the mixture was stirred at room temperature for 4 days. Ice water was added to the reaction mixture, and the resulting mixture was extracted with diethyl ether. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1) to give the title compound (528 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 4 days
  3. extractionthe resulting mixture was extracted with diethyl ether
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-6bae7e8813514a788ba9af6849e38787
Source dataset
uspto-grants-2007_05
Patent number
US07217697B2

Reaction notes

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