Imidazole → HCID 69386265, compound

HRID 916811Notes

Reaction equation

HRID 916811 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=1.N1C=CN=C1>CN(C=O)C>[Si:1]([O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][C:17]([CH3:18])=[O:19])=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride2×HCID 70192744-Hydroxyphenylacetone

Product 1

HCID 69386265HCID 69386265, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of tert-butyldimethylsilyl chloride (13.6 g) in DMF (50 ml) was added dropwise to stirred solution of 4-hydroxyphenylacetone (12.5 g) and imidazole (9.0 g) in DMF (150 ml) at 20° under N2. After 0.67 h additional tert-butyldimethylsilyl chloride (4.7 g) was added and the reaction stirred for 0.75 h. The reaction mixture was concentrated in vacuo and the residue partitioneed between Et2O and water. The organic phase was washed with water, brine, dried (MgSO4) and evaporated to dryness. The residue was purified by chromatography on a Biotage (90 g) eluting with cyclohexane-Et2O (9:1) to give the title compound (17.5 g), ES+ve 282 (M+NH4)+

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried (MgSO4)
  4. customevaporated to dryness
  5. customThe residue was purified by chromatography on a Biotage (90 g)
  6. washeluting with cyclohexane-Et2O (9:1)

Sources & evidence

ORD record
ord-a9728629ad8748ae9cb4d70ffe75312d
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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