Diethyl Ether → HCID 131719365, compound

HRID 1720131Notes

Reaction equation

HRID 1720131 reaction equation
[H-].[Na+].[C:3]([C:5]([C:15]#[N:16])([CH3:14])[C:6]([O:8][CH:9](O)[CH2:10][CH2:11][CH3:12])=[O:7])#[N:4].[C:17]1([Se:23]Br)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])(O)=[O:26].[Na+].[K+].[Br-].[CH3:32][CH2:33]OCC>CN(C)C=O>[C:17]1([Se:23][C:9]2[CH:10]=[CH:11][CH:12]=[CH:33][CH:32]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:3]([C:5]([C:15]#[N:16])([CH3:14])[C:6]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:26])=[O:7])#[N:4]

Participants

8

Reactant 6

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 123446BromoselenobenzeneHCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 22420426HCID 22420426, compound

Product 1

HCID 131719365HCID 131719365, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 500 ml 4-neck flask, equipped with a condenser, mechanical stirrer, thermometer, rubber septum, and nitrogen inlet was added sodium hydride (2.7 g, 105 mmol) and anhydrous dimethyl formamide (200 ml) under nitrogen. Butanediol dicyanopropionate (10 g, 40 mmol) was added over 10 min. at room temperature, and the reaction mixture was stirred for 2 hours. The previously prepared phenylselenium bromide solution was added by syringe and the reaction mixture was stirred for 2.5 hours. The reaction mixture was added to 250 ml each of ether and sat. aq. NaHCO3. The organic layer was washed twice with 250 ml of H2O and once with 250 ml of sat. aq. NaCl . The organic layer was separated, dried (MgSO4), and filtered. Solvent was removed under reduced pressure. Crude Yield=23.4 g (quant.). To the crude product was added 10 ml of ether and the mixture was cooled in an ice bath. The bis-phenylselenide precipitated, was filtered, and washed with 5 ml of cold ether. Yield =6.5 g (29%), M.P.=113° C.; NMR δ (CDCl3) 7.75 (d, 4H), 7.40 (m, 6H), 3.95 (m, 4H), 1.85 (s, 6H), 1.40 (br s, 4H); IR (KBr) 2231, 1730, 1234 cm-1.

Workup

  1. customTo a 500 ml 4-neck flask, equipped with a condenser, mechanical stirrer
  2. stirringthe reaction mixture was stirred for 2.5 hours
  3. washThe organic layer was washed twice with 250 ml of H2O and once with 250 ml of sat. aq. NaCl
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customSolvent was removed under reduced pressure
  8. additionTo the crude product was added 10 ml of ether
  9. temperaturethe mixture was cooled in an ice bath
  10. customThe bis-phenylselenide precipitated
  11. filtrationwas filtered
  12. washwashed with 5 ml of cold ether
  13. customYield =6.5 g (29%), M.P.=113° C.

Sources & evidence

ORD record
ord-9dc962c3f2c74194873687d0b107b223
Source dataset
uspto-grants-1996_04
Patent number
US05504252

Reaction notes

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