L-Prolinamide → 3-Phenyl-2-(Phenylseleno)propionaldehyde

HRID 2427893Notes

Reaction equation

HRID 2427893 reaction equation
N1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3](N)=[O:4].[C:9]1([Se:15]N2C(=O)C3=CC=CC=C3C2=O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[C:7]1([CH2:6][CH:2]([Se:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:3]=[O:4])[CH:8]=[CH:7][CH:6]=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 111306L-ProlinamideHCID 590397N-(Phenylseleno)phthalimide

Product 1

HCID 110225673-Phenyl-2-(Phenylseleno)propionaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

General Procedure B for α-Selenenylation of Aldehyde (Table 9, Entries 11 and 12): To a vial containing an aldehyde (0.25 mmol), and 0.5 mL of anhydrous CH2Cl2 was added catalyst L-prolinamide I (0.005 mmol) at room temperature. The mixture was vigorously stirred for 0.5 h in the presence of 4 Å molecule sieves (40 mg). Then N-(phenylseleno)phthalimide (0.3 mmol) was added. After 0.5 h, the molecule sieves were removed by filtrating paper and then the filtrate was treated with water (5 mL), the solution was extracted with ethyl acetate (3×5 mL). The combined extracts were dried over MgSO4, filtered, and concentrated iii vacuo. The resulting residue was then purified by silica gel chromatography, eluting with EtOAc/Hexane (1/40) to provide a clear oil.

Workup

  1. waitAfter 0.5 h
  2. customthe molecule sieves were removed
  3. filtrationby filtrating paper
  4. additionthe filtrate was treated with water (5 mL)
  5. extractionthe solution was extracted with ethyl acetate (3×5 mL)
  6. dry with materialThe combined extracts were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated iii vacuo
  9. customThe resulting residue was then purified by silica gel chromatography
  10. washeluting with EtOAc/Hexane (1/40)
  11. customto provide a clear oil

Sources & evidence

ORD record
ord-97dab5bf2be94b72b1ab7f51548cc557
Source dataset
uspto-grants-2011_06
Patent number
US07968734B2

Reaction notes

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