Sodium Hydroxide → HCID 67849091, compound

HRID 1033892Notes

Reaction equation

HRID 1033892 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[Cl:39])[C:7](/[CH:10]=[CH:11]/[C:12]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]([O:15]CC)=[O:14])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>C(O)C>[CH2:1]([C:5]1[N:6]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[Cl:39])[C:7](/[CH:10]=[CH:11]/[C:12]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:13]([OH:15])=[O:14])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86747873HCID 86747873, compound

Product 1

HCID 67849091HCID 67849091, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl (E)-4-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2,2-bis(benzyl)-3-butenoate (121 mg) in ethanol (5 mL) was heated to reflux with 10% sodium hydroxide solution (3 mL) for 2 hours. The ethanol was evaporated, water was added and the aqueous layer was extracted with ether. The water layer was acidified to pH 1 with dilute hydrochloric acid solution, extracted with ethyl acetate, dried and concentrated to a solid. Trituration with ether provided 75 mg of the white solid hydrochloride salt of the title compound; mp 184°-185° C.

Workup

  1. customThe ethanol was evaporated
  2. additionwater was added
  3. extractionthe aqueous layer was extracted with ether
  4. extractionextracted with ethyl acetate
  5. customdried
  6. concentrationconcentrated to a solid

Sources & evidence

ORD record
ord-fd306e72c04f4db18656289068033d0a
Source dataset
uspto-grants-1994_05
Patent number
US05312828

Reaction notes

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