Triethylamine → 4-[(5-Formylimidazol-1-yl)methyl]benzonitrile

HRID 443214Notes

Reaction equation

HRID 443214 reaction equation
[C:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12]([CH2:13][OH:14])=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].C(N(CC)CC)C.CCOC(C)=O>CS(C)=O>[C:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12]([CH:13]=[O:14])=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 101982471-(4-Cyanobenzyl)-5-hydroxymethyl-1H-imidazole

Product 1

HCID 106322894-[(5-Formylimidazol-1-yl)methyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of the alcohol from Step D (21.5 g, 101 mol) in DMSO (500 ml) at room temperature was added triethylamine 56 ml, 402 mmol), then SO3 -pyridine complex (40.5 g, 254 mmol). After 45 min, the reaction was poured into EtOAc, washed with water and brine, dried (Na2SO4), and concentrated in vacuo to provide the aldehyde as a white powder which was sufficiently pure without further purification.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b5eea04c267b42069af37b45fdb8d6df
Source dataset
uspto-grants-1999_04
Patent number
US05891889

Reaction notes

Loading…