Triethyl phosphite → Tetraethyl [[2,2'-bipyridine]-4,4'-diylbis(methylene)]bis(phosphonate)

HRID 2080648Notes

Reaction equation

HRID 2080648 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[C:13]([CH2:15]Cl)[CH:12]=[CH:11][N:10]=2)[CH:4]=1.C([O:19][P:20]([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23])C>C(Cl)Cl.CCCCCC>[CH3:23][CH2:22][O:21][P:20]([O:24][CH2:25][CH3:26])([CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[C:13]([CH2:15][P:20]([O:21][CH2:22][CH3:23])([O:24][CH2:25][CH3:26])=[O:19])[CH:12]=[CH:11][N:10]=2)[CH:4]=1)=[O:19]

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 105628114,4'-Bis(chloromethyl)-2,2'-bipyridyl

Product 1

HCID 46911978Tetraethyl [[2,2'-bipyridine]-4,4'-diylbis(methylene)]bis(phosphonate)

Reagents, catalysts & solvents 1

HCID 21226440Methylenechloride HexaneSolvent

Procedure

Compound 5 (2.6 g, 10.3 mmol) was refluxed overnight under N2 in triethylphosphite (50 ml). Excess P(OEt)3 was evaporated and the resulting brown oil was column chromatographed (Al2O3, CH2Cl2/MeOH: 98/2). The yellow oil thus obtained was dissolved in a mixture of CH2Cl2/hexane (1/50 ml) and let stand in the freezer to afford after filtration 4 g (85%) of compound 6 as a slightly yellow crystalline solid.

Workup

  1. customExcess P(OEt)3 was evaporated
  2. customchromatographed (Al2O3, CH2Cl2/MeOH: 98/2)
  3. customThe yellow oil thus obtained
  4. customto afford
  5. filtrationafter filtration 4 g (85%) of compound 6 as a slightly yellow crystalline solid

Sources & evidence

ORD record
ord-06c8ab942aeb4256b202b25ffc42d47b
Source dataset
uspto-grants-2011_04
Patent number
US07932404B2

Reaction notes

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