Ethyl Acetate → HCID 20131183, compound

HRID 845477Notes

Reaction equation

HRID 845477 reaction equation
[OH:1][CH:2]([CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.[OH-].[K+].[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1.C(OCC)(=O)C>CS(C)=O>[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][O:1][CH:2]([CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:3][N:4]2[CH:8]=[CH:7][N:6]=[CH:5]2)=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 699934-Methyloxybenzyl chlorideHCID 20131152HCID 20131152, compound

Product 1

HCID 20131183HCID 20131183, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-[2-Hydroxy-3-(pentoxy)propyl]-1H-imidazole (Example 29b; 2.12 g, 0.01 mol) was added to a stirred suspension of powdered potassium hydroxide (2.24 g, 0.040 mol) in dimethylsulphoxide (10 ml) at 18° C. and stirred for 0.5 hours. 4-Methoxybenzyl chloride was then added and stirring was continued for 2 hours. Ethyl acetate (350 ml) was added and the solution was washed with water and dried (MgSO4). The solvent was evaporated off under reduced pressure and the crude product was purified by column chromatography (silica gel, chloroform) to give 1-[2-[(4-methoxyphenyl)methoxy]-3-(pentoxy)propyl]-1H-imidazole as a pale-yellow oil.

Workup

  1. stirringstirring
  2. waitwas continued for 2 hours
  3. washthe solution was washed with water
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated off under reduced pressure
  6. customthe crude product was purified by column chromatography (silica gel, chloroform)

Sources & evidence

ORD record
ord-89f89644539c4e1dbf97f687487f720a
Source dataset
uspto-grants-1988_07
Patent number
US04758573

Reaction notes

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