Benzaldehyde → HCID 10103442, compound

HRID 899554Notes

Reaction equation

HRID 899554 reaction equation
C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:29](#[N:32])[CH2:30][CH3:31].[CH:33](=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[Cl-].[NH4+]>>[OH:40][CH:33]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH:30]([CH3:31])[C:29]#[N:32]

Participants

5

Reactant 4

HCID 240BenzaldehydeHCID 7854PropionitrileHCID 25517Ammonium ChlorideHCID 742671,2-Bis(diphenylphosphino)ethane2×

Product 1

HCID 10103442HCID 10103442, compoundYield 90%

Procedure

Under an argon atmosphere, CuO(tert-Bu) (0.03 mmol, 60 μL in THF) and 1,2-bis(diphenylphosphino)ethane (hereinafter, referred to as dppe) (18 mg, 0.045 mmol) were mix dried under vacuum for 1 hour. To the residue, dimethylsufoxide (hereinafter, referred to as DMSO) (0.3 mL), propionitrile (0.3 mL), and benzaldehyde (30 μL, 0.3 mmol) were added to start the reaction. After 2 hours, saturated ammonium chloride was added, and the product was extracted with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over sodium sulfate. Filtration, evaporation, and purification by silica gel column chromatography (ethyl acetate/hexane=1/3) gave the product in 90% yield (44 mg). A diastereomeric rate of the obtained compound was determined to be 1.5:1 (syn:anti).

Workup

  1. additionwere mix
  2. customdried under vacuum for 1 hour
  3. additionwere added
  4. customthe reaction
  5. extractionthe product was extracted with ethyl acetate
  6. washThe combined organic layer was washed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. filtrationFiltration, evaporation, and purification by silica gel column chromatography (ethyl acetate/hexane=1/3)
  9. customgave the product in 90% yield (44 mg)

Sources & evidence

ORD record
ord-c795df14a17b43bf9bec2c8e0b635841
Source dataset
uspto-grants-2008_04
Patent number
US07355061B2

Reaction notes

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