Ethanol → HCID 53766880, compound

HRID 1723569Notes

Reaction equation

HRID 1723569 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].[CH:17]([Br:20])(Br)[Br:18].C(O)C.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[Br:18][C:17]1([Br:20])[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

7

Reactant 4

HCID 702EthanolHCID 5558BromoformHCID 14798Sodium HydroxideHCID 54416982HCID 54416982, compound

Product 1

HCID 53766880HCID 53766880, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-vinyloxyimino-3,3-ethylenedioxybutyrate (syn isomer)(15 g) and benzyl-triethylammonium chloride (164 mg) in a mixture of methylene chloride (13 ml), bromoform (11.4 ml) and ethanol (0.65 ml) was added 50% aqueous solution of sodium hydroxide (105 ml) under ice-cooling. The mixture was stirred for 1 hour at the same temperature and allowed to be stirred at ambient temperature overnight. The mixture was extracted with diethyl ether. The extract was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was subjected to column chromatography on silica gel using a mixture of chloroform and ethyl acetate (4:1 V/V) as an eluent to give ethyl 2-(2,2-dibromocyclopropyloxyimino)-3,3-ethylenedioxybutyrate (syn isomer)(15.4 g) as an oil.

Workup

  1. temperaturecooling
  2. stirringto be stirred at ambient temperature overnight
  3. extractionThe mixture was extracted with diethyl ether
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. additiona mixture of chloroform and ethyl acetate (4:1 V/V) as an eluent

Sources & evidence

ORD record
ord-a59ffc1bf565423f84b79dc155df13d9
Source dataset
uspto-grants-1989_08
Patent number
US04861769

Reaction notes

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