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

HRID 1648458Notes

Reaction equation

HRID 1648458 reaction equation
[Si:1]([O:8][C@H:9]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=1)[C:10](OC)=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.O.C(OCC)(=O)C>CCCCCC.C1(C)C=CC=CC=1>[Si:1]([O:8][C@H:9]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=1)[CH:10]=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 21225700DiisobutylaluminumhydrideHCID 54113343Methyl (R)-2-[(tert-butyldimethylsilyl)oxy]-2-(3-chlorophenyl)acetate

Product 1

HCID 11129841(R)-2-[(tert-Butyldimethylsilyl)oxy]-2-(3-chlorophenyl)acetaldehydeYield 23%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent2×

Conditions

Temperature
-60 °C

Procedure

A solution of 26 g of methyl (R)-α-t-butyldimethylsilyloxy-3-chlorophenylacetate [prepared as described in Step (d), above] in a mixture of 1000 ml of anhydrous hexane and 500 ml of dry toluene was cooled to -60° C., and then 124 ml of a 1M solution of diisobutylaluminum hydride in hexane were added dropwise to the cooled solution. The resulting mixture was stirred at the same temperature for 3 hours, after which 10 ml of water were added to it, and the temperature of the mixture was gradually allowed to rise to room temperature. The reaction mixture was then mixed with water and ethyl acetate, after which it was stirred for 30 minutes. Insoluble materials were filtered off using a Celite (trade mark) filter aid, and the ethyl acetate layer was separated from the filtrate and dried over anhydrous sodium sulfate. The ethyl acetate solvent was removed by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel, using a 1:60 by volume mixture of ethyl acetate and hexane as the eluent, to give 5.41 g of the title compound having an Rf=0.36 (thin layer chromatography on silica gel, using a 1:60 by volume mixture of ethyl acetate and hexane as the developing solvent).

Workup

  1. customto rise to room temperature
  2. stirringafter which it was stirred for 30 minutes
  3. filtrationInsoluble materials were filtered off
  4. filtrationfilter aid
  5. customthe ethyl acetate layer was separated from the filtrate
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe ethyl acetate solvent was removed by distillation under reduced pressure
  8. customthe residue was purified by column chromatography through silica gel
  9. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-cf37577ecf6c403b9cc3c69e7fa2e722
Source dataset
uspto-grants-1995_07
Patent number
US05436257

Reaction notes

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