ethyl (S)-alpha-(t-butyldimethylsilyloxy)-alpha-phenylacetate → (S)-alpha-(t-Butyldimethylsilyloxy)-alpha-phenylacetaldehyde

HRID 1682749Notes

Reaction equation

HRID 1682749 reaction equation
[Si:1]([O:8][C@@H:9]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10](OCC)=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>CCCCCC>[Si:1]([O:8][C@@H:9]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH:10]=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 10968419ethyl (S)-alpha-(t-butyldimethylsilyloxy)-alpha-phenylacetateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 11075902(S)-alpha-(t-Butyldimethylsilyloxy)-alpha-phenylacetaldehyde

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

Following a procedure similar to that described in Preparation 25, but using 8.8 g of ethyl (S)-α-(t-butyldimethylsilyloxy)-α-phenylacetate (prepared as described in Preparation 24), 300 ml of dry hexane and 30 ml of a 1M solution of diisobutylaluminum hydride in hexane, and then purifying the reaction product by column chromatography through silica gel, using a 1:60 by volume mixture of ethyl acetate and hexane as the eluent, the title compound was obtained having an Rf=0.29 (thin layer chromatography over silica gel, using a 1:80 by volume mixture of ethyl acetate and hexane as the developing solvent).

Workup

  1. customthat described in Preparation 25
  2. custompurifying the reaction product by column chromatography through silica gel
  3. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-30e3ad79da12441a994592394f5ec6b8
Source dataset
uspto-grants-1997_06
Patent number
US05635534

Reaction notes

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