2,4-Hexadienoic Acid → HCID 73792921, compound

HRID 1939736Notes

Reaction equation

HRID 1939736 reaction equation
[CH3:1][C:2]([CH3:21])=[CH:3][CH2:4][C@@H:5]([OH:20])[C:6]1[C:16](=[O:17])[C:15]2[C:14]([OH:18])=[CH:13][CH:12]=[C:11]([OH:19])[C:10]=2[C:8](=[O:9])[CH:7]=1.C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C.[C:46](O)(=[O:52])[CH:47]=[CH:48][CH:49]=[CH:50][CH3:51]>ClCCl>[C:46]([O:20][CH:5]([C:6]1[C:16](=[O:17])[C:15]2[C:10]([C:8](=[O:9])[CH:7]=1)=[C:11]([OH:19])[CH:12]=[CH:13][C:14]=2[OH:18])[CH2:4][CH:3]=[C:2]([CH3:21])[CH3:1])(=[O:52])[CH:47]=[CH:48][CH:49]=[CH:50][CH3:51]

Participants

6

Reactant 4

HCID 52512,4-Hexadienoic AcidHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 479503Shikonin

Product 1

HCID 73792921HCID 73792921, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

288 mg (1 mmole) of shikonin, 226 mg (1.1 mmole) of dicyclohexylcarbodiimide and 30 mg (0.25 mmole) of dimethylaminopyridine were dissolved in 3 ml of dry dichloromethane. To the resulting solution was added 112 mg (1 mmole) of 2,4-hexadienoic acid at 0° C. under nitrogen gas, and the mixture was stirred for 30 minutes and then at room temperature for further 3 hours. The resulting product was separated and purified according to the procedures as described in Example 1 to obtain 152 mg (Yield: 40%) of the title compound having the following structure as a red precipitate.

Workup

  1. waitat room temperature for further 3 hours
  2. customThe resulting product was separated
  3. custompurified

Sources & evidence

ORD record
ord-8624281608204a2a891edd64273251a3
Source dataset
uspto-grants-1997_12
Patent number
US05696276

Reaction notes

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