Dimethylformamide → HCID 69202581, compound

HRID 2378330Notes

Reaction equation

HRID 2378330 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:11]=[CH:12]/[C:13]#[N:14])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.I[C:16]1[CH:21]=[CH:20][C:19]2[O:22][CH2:23][O:24][C:18]=2[CH:17]=1.CC([O-])=O.[K+].CN(C=O)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC([O-])=O.CC([O-])=O.[Pd+2].CCCCCC.CCOCC>[O:22]1[C:19]2[CH:20]=[CH:21][C:16]([C:11]([C:5]3[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)=[CH:12][C:13]#[N:14])=[CH:17][C:18]=2[O:24][CH2:23]1

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 1386201-Iodo-3,4-methylenedioxybenzeneHCID 517044Potassium AcetateHCID 12018659HCID 12018659, compound

Product 1

HCID 69202581HCID 69202581, compoundYield 31%

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

(E)-3-(3,5-dimethoxy-phenyl)-acrylonitrile (0.4 g, 2.1 mmol), 4-iodo-1,2-(methylenedioxy)benzene (0.75 g, 3 mmol), Pd(OAc)2 (0.047 g, 0.21 mmol), KOAc (0.62 g, 6.3 mmol) and tetrabutylammonium bromide (0.75 g, 2.3 mmol) were placed in a microwave vial, DMF (3 mL) added and the reaction mixture degassed. The vial was placed in the microwave oven (Emrys Optimizer) at 150° C. for 1 hour. The contents were poured into a water-EtOAc mixture (40 mL, 1:1) and filtered through Celite® washing the filtrate with EtOAc. The organic layer was separated and the crude product isolated by CC (silica gel, hexanes:EtOAc, 3:1 to 1:1). Sonication of the purified solid with an ether:hexane mixture yields (E) 3-benzo[1,3]dioxol-5-yl-3-(3,5-dimethoxy-phenyl) -acrylonitrile (0.2 g, 0.65 mmol) in 31% yield: m.p 95-96° C.; 1H NMR (CDCl3) δ 6.85-6.82 (m, 1H, Ar), 6.79-6.78 (m, 2H, Ar), 6.55-6.52 (m, 3H, Ar), 6.01(s, 2H, CH2), 5.63(s, 1H, CH), 3.8 (s, 6H, 2CH3). Anal. Calcd. for C18H15NO4: C, 69.89; H, 4.89; N, 4.53. Found: C, 69.69; H, 5.12; N, 4.46.

Workup

  1. additionadded
  2. customthe reaction mixture degassed
  3. additionThe contents were poured into a water-EtOAc mixture (40 mL, 1:1)
  4. filtrationfiltered through Celite®
  5. washwashing the filtrate with EtOAc
  6. customThe organic layer was separated
  7. customthe crude product isolated by CC (silica gel, hexanes:EtOAc, 3:1 to 1:1)

Sources & evidence

ORD record
ord-674e9f35ca3b4901b0b51ed331567d8b
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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