Hydrochloric Acid → HCID 86638406, compound

HRID 1662866Notes

Reaction equation

HRID 1662866 reaction equation
[CH2:1]([O:3][P:4]([C:9]1[C:13]([P:14]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][S:11][C:10]=1I)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C([Sn](CCCC)(CCCC)[C:28]1[S:29][CH:30]=[CH:31][CH:32]=1)CCC.Cl>CN(C=O)C.[Cu]Cl>[CH2:1]([O:3][P:4]([C:9]1[C:13]([P:14]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][S:11][C:10]=1[C:28]1[S:29][CH:30]=[CH:31][CH:32]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 86638408HCID 86638408, compound

Product 1

HCID 86638406HCID 86638406, compound

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

3,4-bis(diethoxyphosphoryl)-2-iodothiophene and different equivalents of copper(I) chloride (commercially available product) indicated in Table 6 were dissolved in DMF, to which 2-tributylstannylthiophene (1.2 equivalents) was added at room temperature. Thereafter, the reaction mixture was heated to 80° C. and stirred for 8.5 to 11 hours. After the reaction, the reaction mixture was cooled down to room temperature, to which a 0.6 M hydrochloric acid aqueous solution was added, followed by extraction of the resulting product 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:methanol=15:1) to obtain the specified substance.

Workup

  1. additionwas added at room temperature
  2. customAfter the reaction
  3. additionwas added
  4. extractionfollowed by extraction of the resulting product with ethyl acetate
  5. washThe organic phase was washed with a saturated saline solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed
  8. distillationby distilling off under reduced pressure
  9. customthe resulting crude product was purified with a silica gel column (ethyl acetate:methanol=15:1)
  10. customto obtain the specified substance

Sources & evidence

ORD record
ord-f0e7220f03034f70b6d3afe2fd0312c9
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

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