Imidazole → Tert-butyl[4-(iodomethyl)phenoxy]dimethylsilane

HRID 2387668Notes

Reaction equation

HRID 2387668 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:25]I.[Si:27]([O:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39]O)=[CH:37][CH:36]=1)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]>O1CCCC1>[C:30]([Si:27]([O:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][I:25])=[CH:37][CH:36]=1)([CH3:29])[CH3:28])([CH3:33])([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 10014460(4-((Tert-butyldimethylsilyl)oxy)phenyl)methanol

Product 1

HCID 21760231Tert-butyl[4-(iodomethyl)phenoxy]dimethylsilaneYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Triphenyl phosphine (1.32 g, 5.03 mmol), imidazole (370 mg, 5.47 mmol) and iodine (1.16 g, 4.61 mmol) were added to an ice-cooled solution of 4-(tert-butyldimethylsilyloxy)benzyl alcohol [(1 g, 4.19 mmol), Tet. Lett. (2004), 45, 9617] in tetrahydrofuran (50 mL) and the mixture was stirred at 0° C. for 10 minutes and room temperature for 30 minutes. The reaction mixture was then concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was separated, dried over magnesium sulfate and concentrated in vacuo. Purification of the residue by column chromatography on silica gel, eluting with pentane, afforded the title compound in 41% yield, 600 mg.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by column chromatography on silica gel
  7. washeluting with pentane

Sources & evidence

ORD record
ord-fb03a50cdcef4c07a11a5985894d3d7c
Source dataset
uspto-grants-2012_09
Patent number
US08268881B2

Reaction notes

Loading…