Sodium Hydroxide → HCID 54319035, compound

HRID 905083Notes

Reaction equation

HRID 905083 reaction equation
O1CCOCC1.[OH-].[Na+].C([O:17][CH2:18][C@@H:19]1[O:24][C@@H:23]([O:25][CH:26]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:34]=2[Cl:40])[CH2:27][N:28]2[CH:32]=[CH:31][N:30]=[CH:29]2)[CH2:22][CH2:21][CH2:20]1)(=O)C1C=CC=CC=1>O>[OH:17][CH2:18][C@@H:19]1[O:24][C@@H:23]([O:25][CH:26]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:34]=2[Cl:40])[CH2:27][N:28]2[CH:32]=[CH:31][N:30]=[CH:29]2)[CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 54250108HCID 54250108, compound

Product 1

HCID 54319035HCID 54319035, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

90 ml of dioxan and 20 ml of a 25% w/v aqueous solution of sodium hydroxide were added to 9.15 g of 1-[trans-β-(6-benzoyloxymethyltetrahydropyran-2-yloxy)-2,4-dichlorophenethyl]imidazole, and the mixture was refluxed for 6 hours. At the end of this time, the reaction mixture was cooled, diluted with water and extracted with diethyl ether. The ethereal extract was washed with aqueous sodium chloride and dried over anhydrous sodium sulphate, after which the solvent was evaporated off. The residue was purified by column chromatography through silica gel eluted with a 10:20:3 by volume mixture of benzene, ethyl acetate and ethanol, to give 5.34 g of the title compound as a liquid.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. temperatureAt the end of this time, the reaction mixture was cooled
  3. extractionextracted with diethyl ether
  4. extractionThe ethereal extract
  5. washwas washed with aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulphate
  7. customafter which the solvent was evaporated off
  8. customThe residue was purified by column chromatography through silica gel
  9. washeluted with a 10:20:3 by volume mixture of benzene, ethyl acetate and ethanol

Sources & evidence

ORD record
ord-ab80dd1e02d44e67a63b94e69e01afe9
Source dataset
uspto-grants-1983_12
Patent number
US04421758

Reaction notes

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