Ethanol → HCID 15284532, compound

HRID 377677Notes

Reaction equation

HRID 377677 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[Cl:32])[C:7]([CH2:10]OC(=O)C(CC2C=CC=CC=2)C([O-])=O)=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[OH-:33].[K+].O.[CH2:36]([OH:38])[CH3:37]>>[CH2:1]([C:5]1[N:6]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[Cl:32])[C:7]([CH2:10][CH:37]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:36]([OH:33])=[O:38])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14797Potassium HydroxideHCID 86755155HCID 86755155, compound

Product 1

HCID 15284532HCID 15284532, compoundYield 86%

Procedure

A mixture of diethyl [(2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]methyl-2-benzylmalonate (0.72 g, 1.36 mmol), potassium hydroxide (0.83 g, 14.7 mmol), water (15 mL) and ethanol (25 mL) was refluxed for 4 hours. The ethanol was evaporated, the residual aqueous layer was extracted with diethyl ether, and the basic solution was adjusted to pH 3.75 with concentrated hydrochloric acid. The precipitated product was extracted into methylene chloride, dried, and concentrated. This crude product was flash chromatographed on silica gel with 10% methanol in methylene chloride to give 0.51 g (86%) of 3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-benzylpropanoic acid; mp 118-120° C. (from acetone/diethyl ether as the hydrochloride salt).

Workup

  1. temperaturewas refluxed for 4 hours
  2. customThe ethanol was evaporated
  3. extractionthe residual aqueous layer was extracted with diethyl ether
  4. extractionThe precipitated product was extracted into methylene chloride
  5. customdried
  6. concentrationconcentrated
  7. customchromatographed on silica gel with 10% methanol in methylene chloride

Sources & evidence

ORD record
ord-e2b7d6a782964edd9e5c53be9ee14d4d
Source dataset
uspto-grants-2000_02
Patent number
US06028091

Reaction notes

Loading…