Dimethylformamide → HCID 59093769, compound

HRID 2181605Notes

Reaction equation

HRID 2181605 reaction equation
[Li+].CC([N-]C(C)C)C.[CH2:9]1[CH2:13][O:12][CH2:11][CH2:10]1.[Se:14]1C=CC=[C:15]1[C:19]1[Se:20][C:21]([C:24]2[Se:25][CH:26]=[CH:27][CH:28]=2)=[CH:22][CH:23]=1.CN([CH:32]=[O:33])C>C(OCC)(=O)C>[CH:32]([C:26]1[Se:25][C:24]([C:21]2[Se:20][C:19]([C:15]3[Se:14][C:10]([CH:11]=[O:12])=[CH:9][CH:13]=3)=[CH:23][CH:22]=2)=[CH:28][CH:27]=1)=[O:33]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 2724682Lithium diisopropylamideHCID 599441801~2~,2~2~:2~5~,3~2~-Terselenophene

Product 1

HCID 59093769HCID 59093769, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

LDA (1.0 M solution in THE, 1.0 mL) was added to an anhydrous THF solution (4 mL) containing 2,2′:5′,2″-terselenophene (100 mg) under N2 at −78° C. The solution was stirred at −78° C. for 3 h, anhydrous DMF (2 mL) was added, stirred at −78° C. for 1 h, and slowly warmed to room temperature. The reaction solution was diluted with ethyl acetate (100 mL) and washed with H2O (4×100 mL). The organic layer was separated, dried over MgSO4, filtered, and the solvent was removed under vacuum. The residue was chromatographed over silica gel using (5:1) CH2Cl2/ethyl acetate to afford 2,5″-diformyl-5,2′:5′,2″-terselenophene in 75% yield.

Workup

  1. stirringstirred at −78° C. for 1 h
  2. temperatureslowly warmed to room temperature
  3. washwashed with H2O (4×100 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent was removed under vacuum
  8. customThe residue was chromatographed over silica gel using (5:1) CH2Cl2/ethyl acetate

Sources & evidence

ORD record
ord-1a390350463c4746b651013b645d044b
Source dataset
uspto-grants-2005_05
Patent number
US06894039B2

Reaction notes

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