HCID 131718346, compound → HCID 67851960, compound

HRID 486814Notes

Reaction equation

HRID 486814 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=[O:20])[CH:6]=[C:7]([S:14][CH:15]([CH3:19])[C:16]([OH:18])=[O:17])[C:8]2=[O:13]>C(Cl)(Cl)Cl.CC(O)=O.C([O-])(=O)C.[Ag+]>[C:16]([O:18][CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=[O:20])[CH:6]=[C:7]([S:14][CH:15]([CH3:19])[C:16]([OH:18])=[O:17])[C:8]2=[O:13])(=[O:17])[CH3:15]

Participants

5

Reactant 1

HCID 131718346HCID 131718346, compound

Product 1

HCID 67851960HCID 67851960, compound

Reagents, catalysts & solvents 3

HCID 11246Silver acetateCatalystHCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

A mixture of the brominated acid 1b (6 mmol) and silver acetate (2.2 g, 13.2 mmol) is combined in 20 mL of CHCl3 and 40 mL of AcOH, heated at 95° to 100° C. with vigorous stirring overnight. The solvent was evaporated in vacuo, and the residue was poured onto ice water saturated with NaCl. The crude product and AgCl were collected by filtration and washed with water. The solid was then added to a CHCl3, and the insoluble AgCl was removed by filtration. The AgCl was washed with CHCl3 until the washings were colorless. The combined CHCl3 solutions were dried with Na2SO4, concentrated and chromatographed on a silica gel column (C6H6 -CHCl3, 1:1, v/v). To yield (5-acetoxymethyl-1,4-naphthoquinonyl thio)-propionic acid, designated 1c.

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionthe residue was poured onto ice water saturated with NaCl
  3. filtrationThe crude product and AgCl were collected by filtration
  4. washwashed with water
  5. additionThe solid was then added to a CHCl3
  6. customthe insoluble AgCl was removed by filtration
  7. washThe AgCl was washed with CHCl3 until the washings
  8. dry with materialThe combined CHCl3 solutions were dried with Na2SO4
  9. concentrationconcentrated
  10. customchromatographed on a silica gel column (C6H6 -CHCl3, 1:1

Sources & evidence

ORD record
ord-504ae33e5587406fadda6e5c8c2fd0f5
Source dataset
uspto-grants-1994_03
Patent number
US05292873

Reaction notes

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