Sodium Carbonate → 3-Ethyl-1-benzofuran

HRID 2097059Notes

Reaction equation

HRID 2097059 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1I)[CH:2]=[CH:3][CH3:4].C([O-])([O-])=O.[Na+].[Na+].CC([O-])=O.[Na+]>CN(C=O)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:3]([C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH:1]=1)[CH3:4]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 517045Sodium AcetateHCID 614000581-But-2-enyloxy-iodobenzene

Product 1

HCID 141206573-Ethyl-1-benzofuranYield 43%

Reagents, catalysts & solvents 4

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-but-2-enyloxy-iodobenzene (7.60 g, 27.7 mmol) in DMF (46 mL) was added n-Bu4NCl (8.46 g, 30.4 mmol), Pd(OAc)2 (0.338 g, 1.30 mmol), Na2CO3 (6.01 g, 56.7 mmol) and NaOAc (2.77 g, 27.0 mmol). The mixture was heated to reflux under nitrogen atmosphere overnight. The mixture was diluted with EtOAc and washed with water. The combined organics were washed with brine and dried over Na2SO4. Purification by column chromatography (silica gel, hexanes) gave the title compound (1.74 g, 43%) as a yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 7.75 (s, 1H), 7.63-7.61 (m, 1H), 7.55 (t, J=6.6 Hz, 1H), 7.34-7.23 (m, 2H), 2.71-2.63 (m, 2H), 1.28 (t, J=7.5 Hz, 3H); ESI MS m/z 147 (M+H)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under nitrogen atmosphere overnight
  3. washwashed with water
  4. washThe combined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. customPurification by column chromatography (silica gel, hexanes)

Sources & evidence

ORD record
ord-004d0f07a9bc488788dc205b0f2e46c2
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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