Imidazole → ethyl (S)-alpha-(t-butyldimethylsilyloxy)-alpha-phenylacetate

HRID 1901206Notes

Reaction equation

HRID 1901206 reaction equation
[C:1]([O:11][CH2:12][CH3:13])(=[O:10])[C@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].N1C=CN=C1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>CN(C)C=O>[Si:19]([O:3][C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]([O:11][CH2:12][CH3:13])=[O:10])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 6951557ethyl mandelate, (S)-

Product 1

HCID 10968419ethyl (S)-alpha-(t-butyldimethylsilyloxy)-alpha-phenylacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Following a procedure similar to that described in Preparation 23, but using 23.8 g of ethyl (S)-(+)-mandelate, 26.6 g of imidazole, 400 ml of dimethylformamide, 30.1 g of t-butyldimethylsilyl chloride and 100 ml of dimethylformamide, the title compound was obtained as a liquid, boiling at 125.5°/3.0 mmHg (400 Pa).

Workup

  1. customthat described in Preparation 23

Sources & evidence

ORD record
ord-7b974635fbb149f2a2a52005bddb2e1e
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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