Dimethylformamide → HCID 58438770, compound

HRID 217422Notes

Reaction equation

HRID 217422 reaction equation
Br[C:2]1[S:6][C:5]([CH2:7][O:8][C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[C:14]([CH:19]=[O:20])[CH2:15][O:16]3)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])(O)=O.[Na+].CCOC(C)=O.[CH3:38][N:39](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:19]([C:14]1[CH2:15][O:16][C:17]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([O:8][CH2:7][C:5]1[S:6][C:2]([C:38]#[N:39])=[C:3]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:4]=1)[CH:18]=2)=[O:20]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 58439112HCID 58439112, compound

Product 1

HCID 58438770HCID 58438770, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

7-[(5-Bromo-4-phenyl-2-thienyl)methoxy]-2H-chromene-3-carbaldehyde (120 mg) was dissolved in DMF (2.4 mL). To this reaction liquid were added Zn(CN)2 (65 mL) and Pd(PPh3)4 (65 mg) at room temperature. The reaction mixture was stirred at 100° C. for 5 hours and then poured into 1:1 a mixed vehicle of aqueous NaHCO3 and EtOAc, followed by stirring for 1 hour. The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure, followed by purification by silica gel column chromatography (hexane:EtOAc=100:0 to 70:30) to obtain 5-{[(3-formyl-2H-chromen-7-yl)oxy]methyl}-3-phenylthiophene-2-carbonitrile (83 mg) as a pale yellow solid.

Workup

  1. customTo this reaction liquid
  2. stirringby stirring for 1 hour
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customfollowed by purification by silica gel column chromatography (hexane:EtOAc=100:0 to 70:30)

Sources & evidence

ORD record
ord-c8d94431e9d34a6eb238fbc5be5f5809
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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