Tetrahydrofuran → 4-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehyde

HRID 1953381Notes

Reaction equation

HRID 1953381 reaction equation
[CH2:1]1[CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Na+].[H][H].[CH3:10][C:11]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])[CH3:12]>CCOC(C)=O>[Si:14]([O:4][C:3]1[CH:2]=[CH:1][C:2]([CH:3]=[O:4])=[CH:1][CH:5]=1)([C:11]([CH3:13])([CH3:12])[CH3:10])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 108791334-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehyde

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a dry 100 ml round bottom flask was added 1.31 g of 2. To this was added 50 ml of dry THF, followed by the careful addition of 298 mg NaH (H2 is evolved). After evolution of hydrogen ceased, 1.93 g of TBSCl was added. The reaction was allowed to stir overnight. The solution was then diluted with 100 ml EtOAc, and washed sequentially with water and then brine. The organic layer was then dried with MgSO4 and the solvent removed by evaporation. NMR on the crude product corresponded with the protected aldehyde 4.

Workup

  1. washwashed sequentially with water
  2. dry with materialThe organic layer was then dried with MgSO4
  3. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-c61c002078eb40d9a0ac6f5e3c794480
Source dataset
uspto-grants-2000_09
Patent number
US06117845

Reaction notes

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