Sodium Iodide → HCID 86757229, compound

HRID 1388038Notes

Reaction equation

HRID 1388038 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4](C(OC)=O)[CH:3]=1.Cl[CH2:22][CH2:23][O:24][CH2:25][CH2:26]Cl.[C:28](=[O:31])([O-])[O-].[K+].[K+].[I-].[Na+].CN([CH:39]=[O:40])C>>[CH3:39][O:40][CH:4]1[C:3](=[C:28]=[O:31])[C:2]([N:1]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:16][CH:15]=[C:5]1[O:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 8115Bis(2-chloroethyl) etherHCID 11430Potassium CarbonateHCID 18472387HCID 18472387, compound

Product 1

HCID 86757229HCID 86757229, compound

Conditions

Temperature
70 °C

Procedure

A mixture of ethyl 4-(4-amino-2-methoxycarbonyl-phenoxy)butyrate (2.20 g), bis(2-chloroethyl)ether (0.915 ml, 7.81 mmol), potassium carbonate(3.24 g, 23.4 mmol), sodium iodide (2.34 g, 15.6 mmol) and DMF (20 ml) was stirred at 70° C. for 24 hours, and the mixture was concentrated under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl acetate. The organic, layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified with column chromatography (silica gel 30 g, ethyl acetate/hexane=1/4), and the desired fraction was concentrated under reduced pressure to give ethyl 4-(2-methoxy-carbonyl-4-morpholinophenoxy)butyrate (2.18 g).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionTo the residue was added water
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic, layer was dried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified with column chromatography (silica gel 30 g, ethyl acetate/hexane=1/4)
  7. concentrationthe desired fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bbfecbb280d6487abcf237c068d3c3fe
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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