Imidazole → tert-Butyl[(5-iodopentyl)oxy]dimethylsilane

HRID 1369124Notes

Reaction equation

HRID 1369124 reaction equation
N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:25]I.[Si:27]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]O)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].[O-]S([O-])=O.[Na+].[Na+]>C(#N)C.C1(C)C=CC=CC=1>[Si:27]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][I:25])([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]

Participants

8

Reactant 5

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 24437Sodium SulfiteHCID 36143185-((Tert-butyldimethylsilyl)oxy)pentan-1-ol

Product 1

HCID 14567006tert-Butyl[(5-iodopentyl)oxy]dimethylsilaneYield 69%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

To a mixture of imidazole (1.13 g, 16.6 mmol), triphenyl phosphine (2.16 g, 8.24 mmol), and iodine (1.92 g, 7.56 mmol) in a mixed solvent of toluene (40 mL) and acetonitrile (4 mL) was added 5-t-butyldimethylsilyloxy-1-pentanol (1.5 g, 6.87 mmol). The mixture was stirred for 1 h at room temperature and aqueous Na2SO3 was added. The mixture was extracted with ethyl acetate and the extracts were dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography with 10:1 hexane/ethyl acetate to give the title compound (1.55 g, 69%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialthe extracts were dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography with 10:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-8181fbfa95274f9fb79bac6e744ecbf9
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

Loading…