Sodium Bicarbonate → 4-Chloro-1-(4-chlorophenoxy)-3,3-dimethyl-1-(imidazol-1-yl)-butan-2-ol

HRID 127243Notes

Reaction equation

HRID 127243 reaction equation
C1(S(O)(=O)=O)C2C=CC=C(S(O)(=O)=O)C=2C=CC=1.[Cl:19][CH2:20][C:21]([CH3:39])([CH3:38])[C:22](=[O:37])[CH:23]([O:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)[N:24]1[CH:28]=[CH:27][N:26]=[CH:25]1.C(=O)(O)[O-].[Na+].[BH4-].[Na+]>C(Cl)Cl.C(O)(C)C>[Cl:19][CH2:20][C:21]([CH3:39])([CH3:38])[CH:22]([OH:37])[CH:23]([O:29][C:30]1[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=1)[N:24]1[CH:28]=[CH:27][N:26]=[CH:25]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 20286585HCID 20286585, compound2×

Product 1

HCID 202865634-Chloro-1-(4-chlorophenoxy)-3,3-dimethyl-1-(imidazol-1-yl)-butan-2-olYield 75%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

18.8 g (0.04 mol) of 4-chloro-1-(4-chlorophenoxy)-3,3-dimethyl-1-(imidazol-1-yl)-butan-2-one naphthalene-1,5-disulphonate [=Compound 15; prepared in accordance with Example 1, in 81% yield] were suspended in 100 ml of methylene chloride and 100 ml of sodium bicarbonate solution were added. The organic phase was separated off, dried over sodium sulphate and concentrated by distilling off the solvent in vacuo. The base thus obtained was taken up in 100 ml of isopropanol and 2 g (0.05 mol) of sodium borohydride were introduced incrementally at 5° to 10° C. The mixture was stirred for 15 hours at room temperature and the isopropanol was then distilled off. The residue was taken up in 100 ml of methylene chloride and, after adding 100 ml of water, was stirred for a further 15 hours at room temperature. The organic phase was then separated off, washed twice with 50 ml of water at a time, dried over sodium sulphate and concentrated. The oil which remained was boiled up in 100 ml of petroleum ether, which caused it to crystallize. 9.8 g (75% of theory) of 4-chloro-1-(4-chlorophenoxy)-3,3-dimethyl-1-(imidazol-1-yl)-butan-2-ol were obtained as an isomer mixture (erythro form and threo form) of melting point 120°-125° C.

Workup

  1. customThe organic phase was separated off
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated
  4. distillationby distilling off the solvent in vacuo
  5. customThe base thus obtained
  6. distillationthe isopropanol was then distilled off
  7. additionafter adding 100 ml of water
  8. stirringwas stirred for a further 15 hours at room temperature
  9. customThe organic phase was then separated off
  10. washwashed twice with 50 ml of water at a time
  11. dry with materialdried over sodium sulphate
  12. concentrationconcentrated
  13. customto crystallize

Sources & evidence

ORD record
ord-421b56e5e8a946b9ad493d608f0a5701
Source dataset
uspto-grants-1981_03
Patent number
US04255434

Reaction notes

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