Hydride → (R)-2-[(tert-Butyldimethylsilyl)oxy]-2-(3-chlorophenyl)acetaldehyde

HRID 1004073Notes

Reaction equation

HRID 1004073 reaction equation
C[O:2][C:3](=O)[C@@H:4]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1)[O:5][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[H-]>CCOCC.C1(C)C=CC=CC=1>[Cl:19][C:15]1[CH:14]=[C:13]([C@@H:4]([O:5][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:7])[CH3:8])[CH:3]=[O:2])[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 166653HydrideHCID 54113343Methyl (R)-2-[(tert-butyldimethylsilyl)oxy]-2-(3-chlorophenyl)acetate

Product 1

HCID 11129841(R)-2-[(tert-Butyldimethylsilyl)oxy]-2-(3-chlorophenyl)acetaldehydeYield 85.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of (R)-(3-chloro-phenyl)-(tert-butyl-dimethyl-silanoxy)-acetic acid methyl ester (4.0 g) in anhydrous ether (10 ml) and maintained at <-65° was added dropwise a 1.5M solution of di-isobututylaluminium hydride in toluene (10 ml). When addition was complete the solution was stirred at -65° for a further hour, then quenched with methanol (10 ml). The mixture was allowed to attain room temperature when silica (20 g) was added. Solvent was removed under reduced pressure, and the residue was purified by flash chromatography, eluting with cyclohexane:ethyl acetate (9:1) to give the title compound as a colourless liquid (3.1 g).

Workup

  1. additionWhen addition
  2. customquenched with methanol (10 ml)
  3. customto attain room temperature
  4. additionwas added
  5. customSolvent was removed under reduced pressure
  6. customthe residue was purified by flash chromatography
  7. washeluting with cyclohexane:ethyl acetate (9:1)

Sources & evidence

ORD record
ord-fc4c706520c747848a8fe1c9ff40bd58
Source dataset
uspto-grants-2000_04
Patent number
US06048872

Reaction notes

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