Ethanol → HCID 9948737, compound

HRID 354230Notes

Reaction equation

HRID 354230 reaction equation
[CH3:1][CH:2]1[C:7]2(Cl)[C:8](=[O:9])[C:4]([Cl:13])([C:5]([Cl:12])=[C:6]2Cl)[CH:3]1[C:14]1[O:18][N:17]=[C:16]([CH3:19])[CH:15]=1.[CH3:20][CH2:21][O-].[Na+].C([OH:26])C>>[Cl:13][C:4]1[C:5]([Cl:12])=[CH:6][C:7]([C:8]([O:9][CH2:20][CH3:21])=[O:26])=[C:2]([CH3:1])[C:3]=1[C:14]1[O:18][N:17]=[C:16]([CH3:19])[CH:15]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 12993786HCID 12993786, compound

Product 1

HCID 9948737HCID 9948737, compound

Procedure

0.11 g of 6-methyl-5-(3-methylisoxazol-5-yl)-1,2,3,4-tetrachlorobicyclo[2.2.1]hept-2en-7-one (a mixture of trans:cis=1:1) was dissolved in 1 ml of ethanol, and 0.06 g of sodium ethylate was added, while cooling with ice. The resulting solution was stirred for an hour at room temperature. The reaction solution was poured into 50 ml of ice-water, and extracted with 30 ml of ethyl acetate twice. The organic layer was washed with saturated salt water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The obtained viscous liquid was purified on silica gel column chromatography (elution with n-hexane/ethyl acetate) to give 0.024 g of the title compound as white crystals. Melting point 86-88° C.

Workup

  1. temperaturewhile cooling with ice
  2. extractionextracted with 30 ml of ethyl acetate twice
  3. washThe organic layer was washed with saturated salt water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe obtained viscous liquid was purified on silica gel column chromatography (elution with n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2475cc011f924869915d7243da40fe20
Source dataset
uspto-grants-2004_06
Patent number
US06756497B1

Reaction notes

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