Imidazole → HCID 19904717, compound

HRID 2372534Notes

Reaction equation

HRID 2372534 reaction equation
[CH3:1][CH:2]([OH:7])[CH2:3][CH:4]([OH:6])[CH3:5].[Si:8](Cl)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].N1C=CN=C1>CN(C)C=O.CCOCC>[Si:8]([O:6][CH:4]([CH3:5])[CH2:3][CH:2]([OH:7])[CH3:1])([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 122622,4-PentanediolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 19904717HCID 19904717, compoundYield 56.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.00 g (9.60 mmol) 2,4-pentanediol in 9 mL dimethylformamide was added 1.52 g (10.1 mmol) t-butyldimethylsilyl chloride and 915 mg (13.4 mmol) imidazole. The solution was stirred for 12 hrs, diluted in 100 mL of ether, and washed 5 ×, each with 2 mL water. The organic phase was dried over MgSO4, filtered, and concentrated. Chromatography on a 2×18 cm column, packed with hexane and eluted with 100 mL each of 5%, 10%, and 25% ethyl acetate/hexane provided 1.192 g of a clear colorless oil in 10 mL fractions 6-14.

Workup

  1. washwashed 5 ×
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washeluted with 100 mL each of 5%, 10%, and 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-6b2bcca75daf404daa1a7f0c9a39168d
Source dataset
uspto-grants-1992_03
Patent number
US05099020

Reaction notes

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