HCID 59155854, compound → HCID 59155811, compound

HRID 1662890Notes

Reaction equation

HRID 1662890 reaction equation
[CH2:1]([O:5][P:6]([C:13]1[CH:17]=[C:16]([I:18])[S:15][C:14]=1I)([O:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:7])[CH2:2][CH2:3][CH3:4].C([Li])CCC.P([O-])([O-])(O)=O.[Na+].[Na+].P([O-])(O)(O)=O.[Na+]>C1COCC1>[CH2:9]([O:8][P:6]([C:13]1[CH:17]=[C:16]([I:18])[S:15][CH:14]=1)([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:7])[CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 59155854HCID 59155854, compoundHCID 86630341Sodium phosphate (Na3(PO4)2)HCID 178418339Butyllithium

Product 1

HCID 59155811HCID 59155811, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

In THF, 3.10 g (5.9 mmols) of 3-(dibutoxyphosphoryl)-2,5-diiodothiophene was dissolved and cooled down to −78° C. Commercially available n-butyl lithium (1.59 M hexane solution, 6.2 mmols) was slowly dropped, followed by stirring for 1 hour at a standing temperature. Thereafter, a disodium hydrogen phosphate/sodium dihydrogen phosphate buffer solution, adjusted to pH=7, was added, followed by extraction with ethyl acetate. The organic phase was washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was removed by distilling off under reduced pressure, and the resulting crude product was purified with a silica gel column (ethyl acetate:hexane=1:1) to obtain the specified substance in the form of a brown oil at a yield of 1.88 g (yield: 79%). The thus obtained substance was used as it is for reaction in Example 12(18).

Workup

  1. additionwas added
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic phase was washed with a saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed
  6. distillationby distilling off under reduced pressure
  7. customthe resulting crude product was purified with a silica gel column (ethyl acetate:hexane=1:1)
  8. customto obtain the specified substance in the form of a brown oil at a yield of 1.88 g (yield: 79%)
  9. customis for reaction in Example 12(18)

Sources & evidence

ORD record
ord-f3c533a285254339837b4f90bdf1e43d
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

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