Triethylamine → (S)-(+)-3-(t-butyldimethylsilyloxy)-2-methylpropanal

HRID 329786Notes

Reaction equation

HRID 329786 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]([CH3:13])[CH2:11][OH:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.S(=O)(=O)=O.P([O-])(O)(O)=O.[K+]>CS(C)=O>[Si:1]([O:8][CH2:9][C@H:10]([CH3:13])[CH:11]=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24682Sulfur trioxideHCID 516951Monobasic potassium phosphateHCID 10998135(2R)-3-[(tert-butyldimethylsilyl)oxy]-2-methylpropan-1-ol

Product 1

HCID 10241965(S)-(+)-3-(t-butyldimethylsilyloxy)-2-methylpropanalYield 82.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

(R)-(+)-3-(t-Butyldimethylsilyloxy)-2-methyl-1-propanol (3.0 g; 14.7 mmol) was added to a mixture of dimethylsulfoxide (20 ml) and triethylamine (13.4 ml), and a solution of the pyridine complex of sulfur trioxide (6.9 g; 43.3 mmol) in dimethylsulfoxide (20 ml) was added thereto at a temperature below 20° C. under stirring. Stirring was continued for 10 minutes, and an aqueous solution (80 ml) of 2M potassium dihydrogenphosphate and ice (40 g) were added thereto to stop the reaction. Insoluble materials were removed by filtration, and the filtrate was extracted with hexane (100 ml) three times. The organic layer was washed successively with water and aqueous sodium chloride and dried over anhydrous sodium sulfate. Removal of the solvent by distillation under reduced pressure gave (S)-(+)-3-(t-butyldimethylsilyloxy)-2-methylpropanal (2.46 g; yield, 81%) as a colorless oil. The NMR spectrum of this product was identical to that of the product as obtained in Reference Example 2-1.

Workup

  1. stirringStirring
  2. customthe reaction
  3. customInsoluble materials were removed by filtration
  4. extractionthe filtrate was extracted with hexane (100 ml) three times
  5. washThe organic layer was washed successively with water and aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customRemoval of the solvent
  8. distillationby distillation under reduced pressure

Sources & evidence

ORD record
ord-1b6ef10ebd3a482ba3f2b8da8b0223fd
Source dataset
uspto-grants-1990_01
Patent number
US04892961

Reaction notes

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