Acetonitrile → 3-(1-Tritylimidazol-4-YL) propionaldehyde

HRID 1067718Notes

Reaction equation

HRID 1067718 reaction equation
[C:1]1([C:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][OH:16])[N:10]=[CH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH+]1([O-])CCOCC1.C(#N)C>[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC.ClCCl>[C:23]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][CH:15]=[O:16])[N:10]=[CH:9]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 108328403-(1-Trityl-1H-imidazol-4-YL)propan-1-OLHCID 15900019Morpholine oxide

Product 1

HCID 114514283-(1-Tritylimidazol-4-YL) propionaldehyde

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1 g (2.72 mmol) of 1-(triphenylmethyl)-4-[3-hydroxypropyl]imidazole, 0.55 g (4.07 mmol; 1.5 equivalents) of morpholine oxide and 1.36 g of powdered 4 Å molecular sieve in an anhydrous mixture of acetonitrile and dichloromethane (10:4) is stirred at room temperature under nitrogen. 0.047 g (0.135 mmol; 5 mol %) of tetrapropylammonium perruthenate (VII) is added in a single portion and the mixture is stirred at room temperature for 48 hours. The reaction mixture is filtered through silica gel (preloaded with ethyl acetate) and the filtrate is evaporated under reduced pressure. The oil obtained is purified by chromatography on a column of silica gel with diethyl ether as eluent to yield 3-(1-triphenylmethyl-4-imidazolyl)propionaldehyde.

Workup

  1. stirringthe mixture is stirred at room temperature for 48 hours
  2. filtrationThe reaction mixture is filtered through silica gel (preloaded with ethyl acetate)
  3. customthe filtrate is evaporated under reduced pressure
  4. customThe oil obtained
  5. customis purified by chromatography on a column of silica gel with diethyl ether as eluent

Sources & evidence

ORD record
ord-326bf22cd354482595566b402f0768c7
Source dataset
uspto-grants-2001_06
Patent number
US06248765B1

Reaction notes

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