Imidazole → 1-(4-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)-2-phenylethan-1-one

HRID 2378043Notes

Reaction equation

HRID 2378043 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])=[CH:4][CH:3]=1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].N1C=CN=C1>C1COCC1>[C:20]([Si:17]([CH3:19])([CH3:18])[O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:9])[CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:6][CH:7]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 75607Benzyl 4-hydroxyphenyl ketone

Product 1

HCID 598575951-(4-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)-2-phenylethan-1-oneYield 10.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution consisting of benzyl 4-hydroxyphenyl ketone (650 g) in THF (5.5 L) at room temperature under a nitrogen atmosphere is added tert-butyldimethylsilyl chloride (692 g, 4.59 moles) and imidazole (354 g,). The reaction mixture is stirred overnight and is then concentrated under reduced pressure. The evaporate is dissolved in ether is washed with water and brine, is dried over anhydrous Na2SO4, and is concentrated under reduced pressure to afford a solid. The solid is triturated with pentane. The triturated solids are collected by filtration to afford a solid (850 g.) The filtrate is concentrated under reduced pressure to give a solid. This solid is triturated with pentane and the resulting solids are collected by filtration to provide a second crop of solid (108 g), which afforded a total of 958 g of Compound A.

Workup

  1. concentrationis then concentrated under reduced pressure
  2. dissolutionThe evaporate is dissolved in ether
  3. washis washed with water and brine
  4. dry with materialis dried over anhydrous Na2SO4
  5. concentrationis concentrated under reduced pressure
  6. customto afford a solid
  7. customThe solid is triturated with pentane
  8. filtrationThe triturated solids are collected by filtration
  9. customto afford a solid (850 g.) The filtrate
  10. concentrationis concentrated under reduced pressure
  11. customto give a solid
  12. customThis solid is triturated with pentane
  13. filtrationthe resulting solids are collected by filtration

Sources & evidence

ORD record
ord-c423959cb3c14b219eca241b52fa02d9
Source dataset
uspto-grants-2008_12
Patent number
US07470715B2

Reaction notes

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