Diiodomethane → HCID 23445035, compound

HRID 433619Notes

Reaction equation

HRID 433619 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([N:9]2[CH:13]=[C:12]([CH2:14][OH:15])[N:11]=[CH:10]2)[CH:6]=[CH:7][CH:8]=1)=[CH2:2].[CH2:16]([Zn]CC)C.ICI>C1(C)C=CC=CC=1.CCCCCC>[CH:1]1([C:3]2[CH:4]=[C:5]([N:9]3[CH:13]=[C:12]([CH2:14][OH:15])[N:11]=[CH:10]3)[CH:6]=[CH:7][CH:8]=2)[CH2:16][CH2:2]1

Participants

6

Reactant 3

HCID 6346DiiodomethaneHCID 23445130HCID 23445130, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 23445035HCID 23445035, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
20 °C

Procedure

Under an Ar atmosphere, a mixture of [1-(3-vinyl-phenyl)-1H-imidazol-4-yl]-methanol (0.10 g, 0.5 mmol) in toluene (20 ml) was successively treated with diethylzinc (3.8 ml of a 1.1 M solution in hexane, 4.2 mmol) and diiodomethane (6.6 g, 25 mmol). The resulting mixture was stirred at 20° C. for 12 h. The preciptate was filtered and stirred for 30 min with AcOEt and saturated aqueous NH4Cl solution. The organic phase was separated, dried (Na2SO4) and concentrated to yield the title compound as a yellow oil (0.10 g, 93%). MS: m/e=215 (M+H+).

Workup

  1. filtrationThe preciptate was filtered
  2. stirringstirred for 30 min with AcOEt and saturated aqueous NH4Cl solution
  3. customThe organic phase was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c0ab51ad48634e4d893452d0874310ea
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Reaction notes

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