Acetonitrile → HCID 18320530, compound

HRID 370307Notes

Reaction equation

HRID 370307 reaction equation
[CH3:1][O:2][CH:3]([O:23][CH3:24])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7](OS(C(F)(F)F)(=O)=O)=[C:6]([O:21][CH3:22])[CH:5]=1.CC#N>CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:24][O:23][CH:3]([O:2][CH3:1])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]([O:21][CH3:22])[CH:5]=1

Participants

6

Reactant 2

HCID 6342AcetonitrileHCID 18320524HCID 18320524, compound

Product 1

HCID 18320530HCID 18320530, compoundYield 35.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

5-Nitrophenyl triflate 26 (7 g, 18.7 mmol), palladium (II) acetate (88 mg, 0.39 mmol), 1,1'-bis(diphenylphosphino)ferrocene (430 mg, 0.78 mmol) and hplc grade CH3CN (10 ml) were mixed well in a teflon-lined stainless steel bomb. After adding freshly made, pulverized proton sponge formate (5.1 g, 19.6 mmol), the bomb was sealed and heated at 90° C. for 2 h. The reaction mixture was taken up in EtOAc, passed through a silica gel plug, and then purified on a silica gel column, eluting with 0-30% EtOAc/hexanes to yield 1.5 g (35%) methoxynitrobenzaldehyde acetal 27.

Workup

  1. additionAfter adding freshly
  2. customthe bomb was sealed
  3. custompurified on a silica gel column
  4. washeluting with 0-30% EtOAc/hexanes

Sources & evidence

ORD record
ord-32303edb3307414693b14f50ab726399
Source dataset
uspto-grants-2000_10
Patent number
US06140495

Reaction notes

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