2,6-Dihydroxyanthraquinone → HCID 53655413, compound

HRID 1600473Notes

Reaction equation

HRID 1600473 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

HCID 67762,6-DihydroxyanthraquinoneHCID 11430Potassium CarbonateHCID 14411016Diethyl (4-bromobutyl)phosphonate

Product 1

HCID 53655413HCID 53655413, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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.

Workup

  1. extractionThe solution was extracted with CH2Cl2
  2. dry with materialThe CH2Cl2 solution was dried
  3. customleaving a yellow solid
  4. customThe ester was purified by column chromatography
  5. additionfollowed by addition of water
  6. washThe bisphosphonic acid derivative was washed with CH2Cl2
  7. filtrationfiltered
  8. customcollected

Sources & evidence

ORD record
ord-ad4abfbcf9ae429c9f79a37c477e5d63
Source dataset
uspto-grants-1999_11
Patent number
US05976486

Reaction notes

Loading…