3,3-Diethoxypropyne → HCID 76621209, compound

HRID 1876930Notes

Reaction equation

HRID 1876930 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH:4]([NH:15][C:16](=[O:26])[C:17]1[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=1[CH3:25])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]=[N+:13]=[N-:14])=[CH:8][CH:7]=1.C([O:30][CH:31](OCC)[C:32]#[CH:33])C>O1CCOCC1.O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:27])[CH:4]([NH:15][C:16](=[O:26])[C:17]1[C:18]([CH3:25])=[CH:19][C:20]([CH3:24])=[CH:21][C:22]=1[CH3:23])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH:33]=[C:32]([CH:31]=[O:30])[N:14]=[N:13]2)=[CH:10][CH:11]=1

Participants

6

Reactant 2

HCID 662853,3-DiethoxypropyneHCID 76621205HCID 76621205, compound

Product 1

HCID 76621209HCID 76621209, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

250 mg (0.68 mmol) of (13) and 684 μl (4.77 mmol) of 3,3-diethoxy-propyne were dissolved in 3 ml of dioxane. 500 μl of saturated Cu(AcO)2 solution in H2O were added and the solution was stirred for 10 min. After pouring in ethyl acetate the organic layer was washed with saturated NaHCO3, water, brine and dried over Na2SO4. The crude product was dissolved in 500 μl THF with 10% of HCl and stirred for 1 h. The solution was poured in 20 ml of saturated NaHCO3 solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over Na2SO4. The solvent was removed at the evaporator. The product was used in the next step without further purification.

Workup

  1. washwas washed with saturated NaHCO3, water, brine
  2. dry with materialdried over Na2SO4
  3. dissolutionThe crude product was dissolved in 500 μl THF with 10% of HCl
  4. stirringstirred for 1 h
  5. additionThe solution was poured in 20 ml of saturated NaHCO3 solution
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over Na2SO4
  9. customThe solvent was removed at the evaporator
  10. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-dba35f3df26e4140af37c68c807309c9
Source dataset
uspto-grants-2012_11
Patent number
US08309735B2

Reaction notes

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