Tetrahydrofuran → 3,4-dimethoxy-N-pent-4-enyl-N-phenyl-benzamide

HRID 2207149Notes

Reaction equation

HRID 2207149 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:7].C(=O)([O-])[O-].[Cs+].[Cs+].C1COCC1.Br[CH2:32][CH2:33][CH2:34][CH:35]=[CH2:36]>CCOC(C)=O.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[C:6]([N:8]([CH2:36][CH2:35][CH2:34][CH:33]=[CH2:32])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:7]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 707041-Pentene, 5-bromo-HCID 7369543,4-dimethoxy-N-phenylbenzamide

Product 1

HCID 1185578933,4-dimethoxy-N-pent-4-enyl-N-phenyl-benzamideYield 62%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3,4-dimethoxybenzanilide 33 (1.28 g, 5 mmol) and anhydrous cesium carbonate (4 equiv) in a mixture of anhydrous THF (14 mL) and DMF (56 mL) was added 5-bromo-pent-1-ene (2.85 g, 4 equiv) at room temperature and the mixture was heated at 80° C. for 72 h. The mixture was cooled, taken up in EtOAc and washed twice with water then brine. The organic layer was dried over magnesium sulfate, filtered and concentrated to dryness. The residue was purified by column chromatography on SiO2 (gradient of diethyl ether in petroleum ether) to afford the title compound 37 as a yellow oil (Yield 1.0 g, 62%).

Workup

  1. temperatureThe mixture was cooled
  2. washwashed twice with water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by column chromatography on SiO2 (gradient of diethyl ether in petroleum ether)

Sources & evidence

ORD record
ord-8b7f75d3af0e4ccb804943d63f54bf2d
Source dataset
uspto-grants-2016_06
Patent number
US09376387B2

Reaction notes

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