Sodium Iodide → HCID 86754364, compound

HRID 1584567Notes

Reaction equation

HRID 1584567 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:8]([OH:11])[CH:9]=[CH2:10])[CH:7]=1.[I-].[Na+].[C:17](=[O:20])([O-])[O-].[K+].[K+].S(C1C=CC(C)=CC=1)(OCCC[NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=O)(=O)=O.[C:45](OCC)(=O)[CH3:46]>>[C:34]([O:33][CH:31]([N:30]=[C:17]=[O:20])[CH2:45][CH2:46][O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:8]([OH:11])[CH:9]=[CH2:10])[CH:7]=1)([CH3:35])([CH3:36])[CH3:37]

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 131203023-[(tert-Butoxycarbonyl)amino]propyl 4-methylbenzene-1-sulfonateHCID 22061198HCID 22061198, compound

Product 1

HCID 86754364HCID 86754364, compoundYield 98%

Conditions

Temperature
50 °C

Procedure

1-(5'-Hydroxy-2'-nitrophenyl)-2-propen-1-ol (2.0 g) is dissolved in dry dimethylfornamide (100 ml) and thereto are added sodium iodide (1 equivalent) and potassium carbonate and 3-t-butoxycarbonylaminopropyl tosylate (1.5 equivalent). The mixture is stirred at 50° C. for 6 hours, and thereto is added ethyl acetate. The mixture is washed with an aqueous saturated saline solution, dried over sodium sulfate. After distilling off the solvent, the residue is purified with a silica gel column chromatography to give 1-[5'-(3"-t-butoxy-carbonylaminopropyloxy)-2'-nitrophenyl]-2-propen-1-ol (3.53 g) as pale brown caramel.

Workup

  1. washThe mixture is washed with an aqueous saturated saline solution
  2. dry with materialdried over sodium sulfate
  3. distillationAfter distilling off the solvent
  4. customthe residue is purified with a silica gel column chromatography

Sources & evidence

ORD record
ord-0a1d501cd4e04f188b564e159059638c
Source dataset
uspto-grants-1999_08
Patent number
US05932732

Reaction notes

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