Sodium Iodide → HCID 69140908, compound

HRID 840504Notes

Reaction equation

HRID 840504 reaction equation
Br.[CH3:2][N:3]([CH3:23])[CH2:4][CH2:5][CH2:6][CH:7]1[C:13]2[CH:14]=[CH:15][C:16]([OH:18])=[CH:17][C:12]=2[CH2:11][CH2:10][C:9]2[CH:19]=[CH:20][CH:21]=[CH:22][C:8]1=2.[I-].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+].C1OCCOCCOCCOCCOCCOC1.Br[CH2:51][CH2:52][CH2:53][C:54]([O:56][CH2:57][CH3:58])=[O:55]>CN(C=O)C.CC(C)=O>[CH2:57]([O:56][C:54](=[O:55])[CH2:53][CH2:52][CH2:51][O:18][C:16]1[CH:15]=[CH:14][C:13]2[CH:7]([CH2:6][CH2:5][CH2:4][N:3]([CH3:2])[CH3:23])[C:8]3[CH:22]=[CH:21][CH:20]=[CH:19][C:9]=3[CH2:10][CH2:11][C:12]=2[CH:17]=1)[CH3:58]

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 2855718-Crown-6HCID 76300Ethyl 4-bromobutyrateHCID 22619637HCID 22619637, compound

Product 1

HCID 69140908HCID 69140908, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To 500 mg (1.32 mmol) of 6 was added 10 ml of freshly distilled acetone (distilled over anhydrous K2CO3) and 10 ml of anhydrous DMF. To this reaction mixture was added 450 mg (3.0 mmol) of sodium iodide, 2 g of 4° A molecular sieves, 2 g (6.13 mmol) of cesium carbonate and a catalytic amount of 18-crown-6. To this reaction mixture was added 500 μl (3.38 mmol) of ethyl 4-bromobutyrate and the reaction mixture was heated on an preheated oil bath (90° C.) under argon atmosphere for 18 hours. The mixture was cooled to room temperature and filtered. The residue was washed with 30 ml of chloroform. The combined filtrate was concentrated under reduced pressure and redissolved in 100 ml of dichloromethane. This was washed with 2×100 ml of 5% NaOH followed by 2×100ml of water, dried (Na2SO4) and concentrated. The residue was purified by silica gel column chromatography using 10% methanol in dichloromethane to give 450 mg (1.09 mmol, 83%) of 7 as a brownish oil.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. washThe residue was washed with 30 ml of chloroform
  4. concentrationThe combined filtrate was concentrated under reduced pressure
  5. dissolutionredissolved in 100 ml of dichloromethane
  6. washThis was washed with 2×100 ml of 5% NaOH
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-83a0c29716a040a087d930c1ebcecff9
Source dataset
uspto-grants-2002_04
Patent number
US06368814B1

Reaction notes

Loading…