HCID 14824937, compound → (4-((Tert-butyldimethylsilyl)oxy)phenyl)methanol

HRID 2293587Notes

Reaction equation

HRID 2293587 reaction equation
[Si:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13](OC)=[O:14])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Si:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14824937HCID 14824937, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10014460(4-((Tert-butyldimethylsilyl)oxy)phenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the crude product from Step A dissolved in 150 mL of anhydrous THF was added 50 mL of a 1.0M solution of lithium aluminum hydride in THF at 0° C. under a nitrogen atmosphere. The reaction mixture was allowed to warm to room temperature and was stirred for 2 hours. The reaction was then quenched by sequential addition of 1.90 mL of water, 1.90 mL of 15% aqueous sodium hydroxide, and 5.70 mL water. The granular aluminum salts were separated from the reaction mixture by vacuum filtration through Celite, then the filtrate was evaporated in vacuo. The residue was redissolved in methylene chloride, dried (MgSO4), filtered, and evaporated. Removal of the residual solvent in vacuo afforded 20.290 g (80% two steps) of the title compound as a colorless oil.

Workup

  1. customThe reaction was then quenched by sequential addition of 1.90 mL of water, 1.90 mL of 15% aqueous sodium hydroxide, and 5.70 mL water
  2. customThe granular aluminum salts were separated from the reaction mixture by vacuum filtration through Celite
  3. customthe filtrate was evaporated in vacuo
  4. dissolutionThe residue was redissolved in methylene chloride
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customRemoval of the residual solvent in vacuo

Sources & evidence

ORD record
ord-4e856b23bbc848c1825cf4618606746d
Source dataset
uspto-grants-1997_11
Patent number
US05686478

Reaction notes

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