Acetic Acid → HCID 13176304, compound

HRID 1981307Notes

Reaction equation

HRID 1981307 reaction equation
B([O-])=O.[Na+].[Cl:5][C:6]1[CH:25]=[CH:24][C:9]([O:10][CH:11]([N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)[C:12](=[O:18])[C:13]([CH3:17])([CH3:16])[CH:14]=[CH2:15])=[CH:8][CH:7]=1.C(O)(=O)C>CO>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([O:10][CH:11]([N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)[CH:12]([OH:18])[C:13]([CH3:16])([CH3:17])[CH:14]=[CH2:15])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 145326Sodium metaborateHCID 13176303HCID 13176303, compound

Product 1

HCID 13176304HCID 13176304, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.8 g (0.1 mol) of sodium boranate were introduced in portions into a solution of 15.3 g (0.05 mol) of 5-(4-chlorophenoxy)-3,3-dimethyl-5-(imidazol-1-yl)-pent-1-en-4-one (obtained as described in Example 1) in 150 ml of methanol, the mixture being cooled externally. After 6 hours, the reaction mixture was adjusted to pH 6 with dilute acetic acid, and was concentrated by evaporation under reduced pressure. The residue was taken up in ethyl acetate, and the solution was washed once with dilute sodium bicarbonate solution and three times with water, dried over sodium sulphate and thereafter concentrated in vacuo. The oily residue was dissolved in a small amount of ether and petroleum ether was added to the solution. The resulting precipitate was separated off, washed with a small amount of petroleum ether and dried. 12.2 g (79.7% of theory) of 5-(4-chlorophenoxy)-3,3-dimethyl-5-(imidazol-1-yl)-pent-1-en-4-ol of melting point 88° to 90° C. were obtained.

Workup

  1. temperaturethe mixture being cooled externally
  2. concentrationwas concentrated by evaporation under reduced pressure
  3. washthe solution was washed once with dilute sodium bicarbonate solution and three times with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. dissolutionThe oily residue was dissolved in a small amount of ether and petroleum ether
  7. additionwas added to the solution
  8. customThe resulting precipitate was separated off
  9. washwashed with a small amount of petroleum ether
  10. customdried

Sources & evidence

ORD record
ord-791f1d1c3d534eefae3ae5a71e579261
Source dataset
uspto-grants-1985_04
Patent number
US04514409

Reaction notes

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