Imidazole → HCID 53637572, compound

HRID 1069092Notes

Reaction equation

HRID 1069092 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([OH:14])[C:10]([O:12][CH3:13])=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].N1C=CN=C1>CN(C)C=O>[Si:15]([O:14][C@H:9]([C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=1)[C:10]([O:12][CH3:13])=[O:11])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 54549146HCID 54549146, compound

Product 1

HCID 53637572HCID 53637572, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl (R)-2-(3,5-dichlorophenyl)-2-hydroxyethanoate (10.485 g), tert-butyidimethylsilyl chloride (8.07 g), and imidazole (3.64 g) in N,N-dimethylformamide (50 mL) was stirred under nitrogen for 18 h. Volatiles were then removed under vacuum and the residue was chromatographed on silica gel, eluting with hexanelethyl acetate (20:1) The title compound was obtained as a colorless oil (15.05 g).

Workup

  1. customVolatiles were then removed under vacuum
  2. customthe residue was chromatographed on silica gel
  3. washeluting with hexanelethyl acetate (20:1) The title compound

Sources & evidence

ORD record
ord-3c31d468a27041fb833f68fbf895b491
Source dataset
uspto-grants-2001_06
Patent number
US06251925B1

Reaction notes

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