Dichloromethane → 3-((Tert-butyldimethylsilyl)oxy)propanal

HRID 1729456Notes

Reaction equation

HRID 1729456 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][OH:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(Cl)Cl.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>CCOCC>[Si:1]([O:8][CH2:9][CH2:10][CH:11]=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 40777913-[(Tert-butyldimethylsilyl)oxy]propan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 36623923-((Tert-butyldimethylsilyl)oxy)propanal

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 500 ml round bottom flask was introduced 5.23 g (27.5 mmol) of 3-t-butyldimethylsilyloxypropanol (prepared according to the method of McDougal et al, J. Org. Chem. 1986, 51, 3388), to which was added 175 ml CH2Cl2, and 8.13 g (36.4 mmol, 1.3 eq) of pyridinium chlorochromate. The reaction was stirred 90 minutes, diluted with ether, and filtered through Florisil™. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel using 10% ether in hexane. This afforded 2.63 g (50%) of the product, 3-t-butyldimethylsilyloxypropanal.

Workup

  1. customprepared
  2. filtrationfiltered through Florisil™
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was chromatographed on silica gel using 10% ether in hexane

Sources & evidence

ORD record
ord-4a5105b0a7564180b6d71b22775233cb
Source dataset
uspto-grants-1994_07
Patent number
US05332807

Reaction notes

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