Methanol → 2-((Tert-butyldimethylsilyl)oxy)acetaldehyde

HRID 1492000Notes

Reaction equation

HRID 1492000 reaction equation
[Si:1]([O:8][CH2:9][C:10](OCC)=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].C([Al+]C(C)C)(C)C.CO.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl.CCOCC.[Cl-].[Na+].O>[Si:1]([O:8][CH2:9][CH:10]=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 887MethanolHCID 24436Sodium SulfateHCID 11183578Ethyl [(tert-butyldimethylsilyl)oxy]acetateHCID 21896610Diisopropylaluminium hydride

Product 1

HCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehyde

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 32.7g (0.15 mole) of ethyl t-butyldimethylsilyloxyacetate in 924 ml of methylene chloride a solution of 1M diisopropylaluminum hydride in methylene chloride is added dropwise with stirring at -78° C. over a period of 1/2 h. The mixture is stirred for 45 min and 100 ml of methanol is added dropwise. The mixture is diluted with 3 l of ether, 100 ml of brine and 70 g of sodium sulfate are added and the mixture is stirred at room temperature for 15 h. The solids are filtered, the filtrates are evaporated and the residue is distilled to give t-butyldimethylsilyloxyacetaldehyde, b.p. 65°-75° C. (14 mm/Hg).

Workup

  1. stirringThe mixture is stirred for 45 min
  2. additionare added
  3. stirringthe mixture is stirred at room temperature for 15 h
  4. filtrationThe solids are filtered
  5. customthe filtrates are evaporated
  6. distillationthe residue is distilled

Sources & evidence

ORD record
ord-d001c6e8780e4c918fb40ccda3579107
Source dataset
uspto-grants-1994_12
Patent number
US05371096

Reaction notes

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