Potassium tert-butoxide → HCID 54416982, compound

HRID 1723568Notes

Reaction equation

HRID 1723568 reaction equation
Br[CH2:2][CH2:3][O:4][N:5]=[C:6]([C:12]1([O:17][CH2:16][CH2:15][O:14]1)[CH3:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8].CC(C)([O-])C.[K+]>CS(C)=O.O1CCCC1>[CH:3]([O:4][N:5]=[C:6]([C:12]1([O:14][CH2:15][CH2:16][O:17]1)[CH3:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH2:2]

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 54204946HCID 54204946, compound

Product 1

HCID 54416982HCID 54416982, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(2-bromoethoxyimino)-3,3-ethylenedioxybutyrate (syn isomer)(50 g) in dimethyl sulfoxide (50 ml) was dropwise added potassium tertbutoxide (21.7 g) in tetrahydrofuran (190 ml) under ice-cooling. The mixture was stirred at the same temperature for 10 minutes. The mixture was poured into ice-water and extracted with diethyl ether. The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo to give ethyl 2-vinyloxyimino-3,3-ethylenedioxybutyrate (syn isomer) (35.1 g) as an oil.

Workup

  1. temperaturecooling
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-8e8b0228684a4c969ab6c5d5364ed5b8
Source dataset
uspto-grants-1989_08
Patent number
US04861769

Reaction notes

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