Chloroform → HCID 53818524, compound

HRID 1723570Notes

Reaction equation

HRID 1723570 reaction equation
[CH:1]([O:3][N:4]=[C:5]([C:11]1([O:16][CH2:15][CH2:14][O:13]1)[CH3:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH2:2].[OH-].[Na+].[CH:19]([Cl:22])(Cl)[Cl:20]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(O)C>[Cl:20][C:19]1([Cl:22])[CH2:2][CH:1]1[O:3][N:4]=[C:5]([C:11]1([O:13][CH2:14][CH2:15][O:16]1)[CH3:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 54416982HCID 54416982, compound

Product 1

HCID 53818524HCID 53818524, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-vinyloxyimino-3,3-ethylenedioxybutyrate (syn isomer)(1.15 g) and benzyl-triethylammonium chloride (114 mg) in a mixture of chloroform (2.4 ml) and ethanol (0.05 ml) was added sodium hydroxide (2.4 ml) under ice-cooling. The mixture was stirred at the same temperature for 30 minutes, allowed to be stirred at ambient temperature for 3 hours and finally stirred at 50° C. for an hour. The mixture was poured into ice-water and extracted with diethyl ether. The extract was washed with water, dried over magnesium sulfate and concentrated in vacuo to give ethyl 2-(2,2-dichlorocyclopropyloxyimino)-3,3-ethylenedioxybutyrate (syn isomer)(1.41 g) as an oil.

Workup

  1. temperaturecooling
  2. stirringto be stirred at ambient temperature for 3 hours
  3. stirringfinally stirred at 50° C. for an hour
  4. extractionextracted with diethyl ether
  5. washThe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa33e58c79864bf6b571b4aca9858840
Source dataset
uspto-grants-1989_08
Patent number
US04861769

Reaction notes

Loading…