Sodium Iodide → HCID 67454236, compound

HRID 45221Notes

Reaction equation

HRID 45221 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][CH:6]([C:11](=[O:13])[CH3:12])[C:7]([O:9][CH3:10])=[O:8].C([O-])([O-])=O.[Cs+].[Cs+].[Na+].[I-].Cl.[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29]Cl>CC#N.C(Cl)Cl>[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29][O:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][CH:6]([C:11](=[O:13])[CH3:12])[C:7]([O:9][CH3:10])=[O:8]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 67453530Methyl 2-(3-hydroxybenzyl)-3-oxobutanoate

Product 1

HCID 67454236HCID 67454236, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1.5 g (6.75 mmol) of methyl 2-(3-hydroxybenzyl)-3-oxobutanoate, 6.6 g (20.25 mmol) of anhydrous Cs2CO3, 0.1 g (0.67 mmol) of NaI and 1 g (7.1 mmol) of 2-dimethylaminoethyl chloride hydrochloride in 20 mL of anhydrous CH3CN is heated for 4 hours at 90° C., and then stirred overnight at room temperature. The reaction medium is filtered and then concentrated under reduced pressure. The residue obtained is taken up in DCM (100 mL), washed with brine (30 mL), dried over Na2SO4, filtered, concentrated under reduced pressure and then purified by chromatography on a column of silica gel, eluting with a DCM/MeOH gradient of 0 to 10% MeOH. After concentrating under reduced pressure, 409 mg of methyl 2-{3-[2-(dimethylamino)ethoxy]benzyl}-3-oxobutanoate are obtained in the form of a brown wax.

Workup

  1. filtrationThe reaction medium is filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue obtained
  4. washwashed with brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. custompurified by chromatography on a column of silica gel
  9. washeluting with a DCM/MeOH gradient of 0 to 10% MeOH
  10. concentrationAfter concentrating under reduced pressure, 409 mg of methyl 2-{3-[2-(dimethylamino)ethoxy]benzyl}-3-oxobutanoate
  11. customare obtained in the form of a brown wax

Sources & evidence

ORD record
ord-d9c6956422344fc38369f5fa69245c27
Source dataset
uspto-grants-2013_09
Patent number
US08541455B2

Reaction notes

Loading…