Potassium Iodide → HCID 58398217, compound

HRID 1258380Notes

Reaction equation

HRID 1258380 reaction equation
[OH:1][C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.Br[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[I-].[K+]>C(Cl)(Cl)Cl.[Ag]=O>[O:13]=[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10](=[O:12])[CH:11]=[C:2]1[O:1][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 79177tert-Butyl bromoacetateHCID 178516607HCID 178516607, compound

Product 1

HCID 58398217HCID 58398217, compound

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6212ChloroformSolvent

Procedure

a mixture of 2-hydroxynaphthalene-1,4-dione (6, 0.52 g, 3.0 mmol), tert-butyl 2-bromoacetate (0.78 g, 4.0 mmol), silver oxide (0.93 g, 4.0 mmol) and potassium iodide (0.05 g, 0.3 mmol) were refluxed in 10 ml of chloroform overnight under Ar. The reaction mixture was filtered and washed with DCM (3×20 ml), the filtrate was concentrated and purified with flash chromatography to give compound 7c as a light yellow solid, 13%, m.p.=120-122° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with DCM (3×20 ml)
  3. concentrationthe filtrate was concentrated
  4. custompurified with flash chromatography

Sources & evidence

ORD record
ord-03d67071ee444e47b38ae491831a1df7
Source dataset
uspto-grants-2013_06
Patent number
US08466157B2

Reaction notes

Loading…