Water → Tetraisopropyl (E,E)-farnesylmethylenebisphosphonate

HRID 54912

Reaction equation

HRID 54912 reaction equation
[H-].[Na+].[CH2:3]([P:14](=[O:23])([O:19][CH:20]([CH3:22])[CH3:21])[O:15][CH:16]([CH3:18])[CH3:17])[P:4](=[O:13])([O:9][CH:10]([CH3:12])[CH3:11])[O:5][CH:6]([CH3:8])[CH3:7].[CH2:24](Br)/[CH:25]=[C:26](/[CH2:28][CH2:29]/[CH:30]=[C:31](/[CH2:33][CH2:34][CH:35]=[C:36]([CH3:38])[CH3:37])\[CH3:32])\[CH3:27].O>C(COC)OC>[CH2:24]([CH:3]([P:4](=[O:13])([O:9][CH:10]([CH3:11])[CH3:12])[O:5][CH:6]([CH3:8])[CH3:7])[P:14](=[O:23])([O:15][CH:16]([CH3:18])[CH3:17])[O:19][CH:20]([CH3:22])[CH3:21])/[CH:25]=[C:26](/[CH2:28][CH2:29]/[CH:30]=[C:31](/[CH2:33][CH2:34][CH:35]=[C:36]([CH3:37])[CH3:38])\[CH3:32])\[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74266Tetraisopropyl methylenediphosphonateHCID 5366048(2E,6E)-1-bromo-3,7,11-trimethyldodeca-2,6,10-triene

Product 1

HCID 86750760Tetraisopropyl (E,E)-farnesylmethylenebisphosphonateYield 60.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Oily sodium hydride (60%, 0.24 g) was added to a solution of tetraisopropyl methylenebisphosphonate (3.44 g) in dimethoxyethane (25 ml). The mixture was stirred at room temperature for 1 hour. Then, a solution of (E,E)-farnesyl bromide (1.43 g) in dimethoxyethane (5 ml) was added dropwise at 0° C. The reaction mixture was stirred at room temperature for 1 hour, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried (MgSO4), and then the solvent was distilled off under reduced pressure. The oily residue was subjected to column chromatography on silica gel. Tetraisopropyl (E,E)-farnesylmethylenebisphosphonate (1.67 g, 60.9%) was obtained as an oil from the fractions obtained by elution with ethyl acetate-chloroform (1:1, v/v).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-73a7b1d009aa461cb31c197a6b725fa7
Source dataset
uspto-grants-1997_04
Patent number
US05624917

Linked notes

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