Potassium tert-butoxide → HCID 54416982, compound

HRID 1074326Notes

Reaction equation

HRID 1074326 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-58b9dce256f14953a6e2e1136af1930d
Source dataset
uspto-grants-1990_11
Patent number
US04973699

Reaction notes

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