Imidazole → HCID 71202560, compound

HRID 1844577Notes

Reaction equation

HRID 1844577 reaction equation
[C:1]([Si:5](Cl)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].[OH:19][CH2:20][C@H:21]([CH3:27])[CH2:22][C:23]([O:25][CH3:26])=[O:24].N1C=CN=C1.O>C(Cl)Cl>[Si:5]([O:19][CH2:20][C@H:21]([CH3:27])[CH2:22][C:23]([O:25][CH3:26])=[O:24])([C:1]([CH3:4])([CH3:3])[CH3:2])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 24862358HCID 24862358, compound

Product 1

HCID 71202560HCID 71202560, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl(chloro)diphenylsilane (26.5 g) was added dropwise to a solution of methyl (R)-4-hydroxy-3-methyl-butyrate (11.0 g) and imidazole (8.5 g) in methylene chloride (200 mL) under ice cooling, and the mixture was then stirred at room temperature for 24 hours. Water was added thereto to separate an organic layer. The organic layer was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (eluting solvent: hexane→hexane/ethyl acetate=97/3) to obtain the title compound (29.8 g).

Workup

  1. customto separate an organic layer
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (eluting solvent: hexane→hexane/ethyl acetate=97/3)

Sources & evidence

ORD record
ord-136e5239a2884182a038ce766f549633
Source dataset
uspto-grants-2015_02
Patent number
US08946443B2

Reaction notes

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