2,6-Dihydroxyanthraquinone → HCID 53655413, compound
Reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([OH:17])[CH:10]=3)[C:5](=[O:18])[C:4]=2[CH:3]=1.C([O:21][P:22]([CH2:27][CH2:28][CH2:29][CH2:30]Br)(=[O:26])[O:23]CC)C.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[P:22]([CH2:27][CH2:28][CH2:29][CH2:30][O:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:17][CH2:30][CH2:29][CH2:28][CH2:27][P:22]([OH:21])([OH:23])=[O:26])[CH:10]=3)[C:5](=[O:18])[C:4]=2[CH:3]=1)([OH:26])([OH:23])=[O:21]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2,6-dihydroxyanthraquinone (1.19 g, 4.98 mmol) and diethyl(4-bromobutyl)phosphonate (3.0 g, 10 mmol) were heated at 60 ° C. in 5 ml DMF in the presence of 0.8 g of K2CO3 for 72 hours. The solution was extracted with CH2Cl2. The CH2Cl2 solution was dried, leaving a yellow solid. The ester was purified by column chromatography. The bisphosphonate ester was converted to the acid by overnight stirring with 4-fold excess of bromotrimethylsilane in dry dichloromethane followed by addition of water. The bisphosphonic acid derivative was washed with CH2Cl2, filtered and collected.