Dimethylformamide → HCID 69203598, compound

HRID 2378331Notes

Reaction equation

HRID 2378331 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[CH:11][C:12]#[N:13])=[CH:9][C:4]=2[O:3][CH2:2]1.I[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=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:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)=[CH:11][C:12]#[N:13])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 696764-IodoanisoleHCID 517044Potassium AcetateHCID 5990923-Benzo[1,3]dioxol-5-yl-acrylonitrile

Product 1

HCID 69203598HCID 69203598, compoundYield 32.4%

Reagents, catalysts & solvents 4

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

Procedure

3-Benzo[1,3]dioxol-5-yl-acrylonitrile (9:1 (E):(Z) mixture) (0.3 g, 1.73 mmol), 4-iodo-anisole (0.57 g, 2.43 mmol), Pd(OAc)2 (0.039 g, 0.17 mmol), KOAc (0.5 g, 5.2 mmol) and tetrabutylammonium bromide (0.6 g, 1.9 mmol) were combined in a microwave vial and DMF (3 mL) added, the reaction mixture was then degassed. The reaction vessel was placed in the microwave oven (Emrys Optimizer) at 150° C. for 1 hour. The contents were poured into water, EtOAc mixture (40 mL, 1:1) and filtered through Celite washing with more 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 compound with an ether:hexane mixture yielded (Z) 3-benzo[1,3]dioxol-5-yl-3-(4-methoxy-phenyl)-acrylonitrile (0.16 g, 0.56 mmol) in 32% yield: m.p 80-81° C.; 1H NMR (CDCl3) δ 7.25(d, 2H, Ar), 6.98(dd, 1H, Ar), 6.89-6.86(m, 4H, Ar), 6.03(s, 2H, CH2), 5.56(s, 1H, CH), 3.84 (s, 3H, OCH3); Anal. Calcd for C17H13NO3: C, 73.11; H, 4.69; N, 5.02 Found: C, 73.02; H, 4.90; N, 4.82.

Workup

  1. additionadded
  2. customthe reaction mixture was then degassed
  3. additionThe contents were poured into water, EtOAc mixture (40 mL, 1:1)
  4. filtrationfiltered through Celite
  5. washwashing with more 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-ef0e9c60304f449a9e77e46faa734ad7
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

Loading…