Potassium Hydroxide → HCID 19613993, compound

HRID 1600474Notes

Reaction equation

HRID 1600474 reaction equation
[OH-:1].[K+].[OH:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:14])[CH:10]=2)[CH:5]=1.C([O:17][P:18]([CH2:23][CH2:24][CH2:25][CH2:26]Br)(=[O:22])[O:19]CC)C>C(O)C>[P:18]([CH2:23][CH2:24][CH2:25][CH2:26][O:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:14][CH2:26][CH2:25][CH2:24][CH2:23][P:18]([OH:17])([OH:19])=[O:22])[CH:10]=2)[CH:5]=1)([OH:19])([OH:17])=[O:1]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 935522,6-DihydroxynaphthaleneHCID 14411016Diethyl (4-bromobutyl)phosphonate

Product 1

HCID 19613993HCID 19613993, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1.34 g of KOH in ethanol were added dropwise to a mixture of 2,6-dihydroxynaphthalene (1.6g, 10 mmol) and diethyl(4-bromobutyl)phosphonate (6.0 g, 22 mmol) in ethanol, the mixture was left at room temperature for over night. The product was extracted with CH2Cl2. The CH2Cl2 solution was dried, leaving a brownish 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. waitthe mixture was left at room temperature for over night
  2. extractionThe product was extracted with CH2Cl2
  3. dry with materialThe CH2Cl2 solution was dried
  4. customleaving a brownish solid
  5. customThe ester was purified by column chromatography
  6. additionfollowed by addition of water
  7. washThe bisphosphonic acid derivative was washed with CH2Cl2
  8. filtrationfiltered
  9. customcollected

Sources & evidence

ORD record
ord-e044e952609c43eab740f079d6d0c8e9
Source dataset
uspto-grants-1999_11
Patent number
US05976486

Reaction notes

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