Juglone → HCID 22007291, compound

HRID 323834Notes

Reaction equation

HRID 323834 reaction equation
[Cl:1][CH2:2][CH2:3][C:4](Cl)=[O:5].[OH:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[C:10](=[O:19])[CH:11]=[CH:12][C:13]2=[O:18]>C(N(CC)CC)C>[Cl:1][CH2:2][CH2:3][C:4]([O:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[C:10](=[O:19])[CH:11]=[CH:12][C:13]2=[O:18])=[O:5]

Participants

4

Reactant 2

HCID 3806JugloneHCID 693643-Chloropropionyl chloride

Product 1

HCID 22007291HCID 22007291, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of triethylamine (1.4 ml) and 1.27 g. of 3-chloropropionylchloride in 5 ml. of DCNM was added to a solution of 1.73 g. of 5-hydroxy-1,4-naphthoquinone. The reaction mixture was stirred for 2 hours at room temperature. The solution was filtered and concentrated to a small volume and chromatographed on a silica gel column (ethylacetate-cyclohexane-DCM) to give 741 mg. of desired product.

Workup

  1. additionof DCNM was added to a solution of 1.73 g
  2. filtrationThe solution was filtered
  3. concentrationconcentrated to a small volume
  4. customchromatographed on a silica gel column (ethylacetate-cyclohexane-DCM)
  5. customto give 741 mg

Sources & evidence

ORD record
ord-6d8ecc4e3a064465908b9acb8cf1c3a3
Source dataset
uspto-grants-2001_04
Patent number
US06214969B1

Reaction notes

Loading…