Water → 4-(8-methoxy-2H-chromen-3-ylcarbonyl)morpholine

HRID 460547Notes

Reaction equation

HRID 460547 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[O:11][CH2:10][C:9]([C:13]([OH:15])=O)=[CH:8]2.[CH2:16]([N:18](CC)[CH2:19][CH3:20])[CH3:17].P(C#N)(OCC)(OCC)=[O:24].O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[O:11][CH2:10][C:9]([C:13]([N:18]1[CH2:19][CH2:20][O:24][CH2:17][CH2:16]1)=[O:15])=[CH:8]2

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 27638908-Methoxy-2H-chromene-3-carboxylic acid

Product 1

HCID 107548644-(8-methoxy-2H-chromen-3-ylcarbonyl)morpholine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution (200 ml) of 8-methoxy-2H-chromene-3-carboxylic acid (10.0 g) in DMF were added triethylamine (8.6 ml) and diethyl cyanophosphate (10.0 ml) and the mixture was stirred at room temperature for 3 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/ethyl acetate) to give the title compound (3.5 g) as a brown oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-8139e317c96947d291f59e34795c6afa
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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