Dimethylformamide → HCID 43378102, compound

HRID 2360646Notes

Reaction equation

HRID 2360646 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:11]([O-:14])([O-])=[O:12].[K+].[K+].[CH3:17][CH2:18][CH2:19]CCCC.[CH3:24]N(C=O)C>C(OCC)(=O)C.O>[CH3:24][O:14][C:11](=[O:12])[CH2:17][CH2:18][CH2:19][O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8900HeptaneHCID 111373-NitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 43378102HCID 43378102, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 3-nitrophenol (8.35 g, 60 mmol), in DMF (50 ml) was added K2CO3 (16.56 g, 120 mmol) and methyl 1,4-bromobutyrate (11.95 g, 66 mmol). The reaction was stirred at room temperature for 16 h. The reaction was diluted with ethyl acetate and water. The organic phase was separated and washed with water (2×200 ml). The organic phase was dried with Na2SO4 and concentrated in vacuo. The required ether was isolated following chromatography (ethyl acetate:heptane, 1:9) as a pale yellow solid (12.2 g, 85% yield). LCMS purity 100%, m/z 240 [M++H]+.

Workup

  1. customThe organic phase was separated
  2. washwashed with water (2×200 ml)
  3. dry with materialThe organic phase was dried with Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe required ether was isolated

Sources & evidence

ORD record
ord-c71d5258778d427a9a2950e8f5e34d11
Source dataset
uspto-grants-2014_04
Patent number
US08686032B2

Reaction notes

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