Hydrochloric Acid → HCID 86638415, compound

HRID 1662882Notes

Reaction equation

HRID 1662882 reaction equation
[CH2:1]([O:5][P:6]([C:13]1[CH:17]=[CH:16][S:15][C:14]=1I)([O:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:7])[CH2:2][CH2:3][CH3:4].C([Sn](CCCC)(CCCC)[C:24]1[S:25][CH:26]=[CH:27][C:28]=1[P:29]([O:36][CH2:37][CH2:38][CH2:39][CH3:40])([O:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:30])CCC.Cl>CN(C=O)C.[Cu]Cl>[CH2:1]([O:5][P:6]([C:13]1[CH:17]=[CH:16][S:15][C:14]=1[C:24]1[S:25][CH:26]=[CH:27][C:28]=1[P:29]([O:36][CH2:37][CH2:38][CH2:39][CH3:40])([O:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:30])([O:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 59155822HCID 59155822, compoundHCID 59155872HCID 59155872, compound

Product 1

HCID 86638415HCID 86638415, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 62652Cuprous chlorideSolvent

Conditions

Temperature
80 °C

Procedure

At room temperature, 0.8045 g (2.00 mmols) of 3-(dibutoxyphosphoryl)-2-iodothiophene and 1.1308 g (2.00 mmols) of 2-(tributylstannyl)-3-(dibutoxyphosphoryl)thiophene were dissolved in DMF, to which 0.2376 g (2.40 mmols) of commercially available copper(I) chloride was added at room temperature. Thereafter, the reaction mixture was heated to 80° C. and stirred for 10 hours. After the reaction, the reaction mixture was cooled down to room temperature, to which a 10% hydrochloric acid aqueous solution, 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 (gradiated from ethyl acetate:hexane=1:1 with acetone) to obtain the specified substance in the form of white crystals at a yield of 1.6012 g (yield: 55%).

Workup

  1. additionwas added at room temperature
  2. customAfter the reaction
  3. extractionfollowed by extraction of the resulting product with ethyl acetate
  4. washThe organic phase was washed with a saturated saline solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed
  7. distillationby distilling off under reduced pressure
  8. customthe resulting crude product was purified with a silica gel column (gradiated from ethyl acetate:hexane=1:1 with acetone)
  9. customto obtain the specified substance in the form of white crystals at a yield of 1.6012 g (yield: 55%)

Sources & evidence

ORD record
ord-b5c8c4e7e91b4011b17f3ca37120b304
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

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