Water → HCID 54253782, compound

HRID 1756144Notes

Reaction equation

HRID 1756144 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=O)=[CH:11][N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]1([CH2:28][CH:29]=O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>O1CCCC1.[Ti](Cl)(Cl)(Cl)Cl.[Zn]>[CH2:1]([N:8]1[C:12]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[CH:29][CH2:28][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:11][N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 962WaterHCID 998PhenylacetaldehydeHCID 19916867HCID 19916867, compound

Product 1

HCID 54253782HCID 54253782, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24193Titanium TetrachlorideCatalystHCID 8028TetrahydrofuranSolvent4×

Conditions

Temperature
0 °C

Procedure

Titanium tetrachloride (0,03 mol) is added dropwise to a stirred suspension of zinc powder (0,06 mol) in tetrahydrofuran (30 ml) at -10° C. under dry nitrogen. The mixture is heated to reflux and refluxing is continued for 1 hour. The solution is cooled to 0° C. and 1-benzyl-5-[1-(4-fluorophenyl)-1-oxomethyl]-1H-imidazole (0,005 mol) in tetrahydrofuran (10 ml) and phenylacetaldehyde (0,006 mol) in tetrahydrofuran (10 ml) are added into the mixture, respectively. The mixture is refluxed with stirring for 1 hour. The dark mixture is poured into water (60 ml), tetrahydrofuran is evaporated and the mixture is extracted with methylene chloride (2×100 ml). The methylene chloride solution is washed with 2N sodium hydroxide and water, dried with sodium sulphate and evaporated to dryness. The residue is purified by flash chromatography.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. temperaturerefluxing
  4. temperatureThe mixture is refluxed
  5. customis evaporated
  6. extractionthe mixture is extracted with methylene chloride (2×100 ml)
  7. washThe methylene chloride solution is washed with 2N sodium hydroxide and water
  8. dry with materialdried with sodium sulphate
  9. customevaporated to dryness
  10. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-fad995d9973e42bb8320fc28b18ee043
Source dataset
uspto-grants-1995_08
Patent number
US05439928

Reaction notes

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