Hexane → Tetramethyl m-trimethylsilylphenyl-1-hydroxy-ethylidenebis(phosphonate)

HRID 1265948Notes

Reaction equation

HRID 1265948 reaction equation
[CH3:1][Si:2]([CH3:19])([CH3:18])[C:3]1[CH:4]=[C:5]([CH2:9][C:10]([P:12](=[O:17])([O:15][CH3:16])[O:13][CH3:14])=[O:11])[CH:6]=[CH:7][CH:8]=1.[CH3:20][O:21][P:22]([O-:25])[O:23][CH3:24].C(NCCCC)CCC.CCCCCC>CCOCC>[CH3:19][Si:2]([CH3:1])([CH3:18])[C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:11])([P:22](=[O:25])([O:23][CH3:24])[O:21][CH3:20])[P:12](=[O:17])([O:15][CH3:16])[O:13][CH3:14])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 8148DibutylamineHCID 11208811Dimethyl m-trimethylsilylphenylacetylphosphonateHCID 21884954Dimethylphosphite

Product 1

HCID 11144043Tetramethyl m-trimethylsilylphenyl-1-hydroxy-ethylidenebis(phosphonate)Yield 65.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of dimethyl m-trimethylsilylphenylacetylphosphonate (1.63 g, 5.0 mmol) in Et2O (10 cm3) was added a solution of dimethylphosphite (0.83 g, 7.5 mmol), dibutylamine (0.32 g, 2.5 mmol) and hexane (10 cm3) at 0° C. A white solid began to form after a few minutes. After 20 min the mixture was filtrated to give the title compound (1.34 g, 65%) as a white solid. Recrystallization was achieved by adding water (9.5 cm3) to a solution of the title compound (0.50 g) in acetic acid (0.5 cm3) and then leaving the resulting mixture for several days in the refrigerator. Filtration afforded the bisphosphonate (0.33 g, 66%) as white crystals.

Workup

  1. customto form after a few minutes
  2. filtrationAfter 20 min the mixture was filtrated

Sources & evidence

ORD record
ord-683bb56de6854abcaa398bf071ee310d
Source dataset
uspto-grants-2003_04
Patent number
US06548042B2

Reaction notes

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