HCID 86638407, compound → HCID 86638409, compound

HRID 1662867Notes

Reaction equation

HRID 1662867 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]=[C:31]([P:41]([O:46][CH2:47][CH3:48])([O:43][CH2:44][CH3:45])=[O:42])[C:32]=1[P:33]([O:38][CH2:39][CH3:40])([O:35][CH2:36][CH3:37])=[O:34])CCC>C1COCC1.[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]=[C:31]([P:41]([O:43][CH2:44][CH3:45])([O:46][CH2:47][CH3:48])=[O:42])[C:32]=1[P:33]([O:35][CH2:36][CH3:37])([O:38][CH2:39][CH3:40])=[O:34])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 86638407HCID 86638407, compoundHCID 86638408HCID 86638408, compound

Product 1

HCID 86638409HCID 86638409, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In THF, 0.037 g (0.076 mmols) of the 2-iodo-3,4-bis(diethoxyphosphoryl)thiophene obtained in Example 4 and 0.049 g (0.076 mmols) of the 2-tributylstannyl-3,4-bis(diethoxyphosphoryl)thiophene obtained in Example 5 were dissolved, to which 0.009 g (0.091 mmols) of commercially available copper(I) chloride was added at room temperature. Thereafter, the reaction mixture was heated and stirred for 4 hours under reflex. After the reaction, the reaction mixture was cooled down to room temperature and the resulting solid was removed by celite filtration. The filtrate was distilled off under reduced pressure to remove the solvent, and the resulting crude product was purified with a silica gel column (ethyl acetate:methanol=15:1 to ethyl acetate:methanol=5:1) to obtain the specified substance in the form of a transparent oil at a yield of 0.049 g (yield: 91%).

Workup

  1. additionwas added at room temperature
  2. temperatureThereafter, the reaction mixture was heated
  3. customAfter the reaction
  4. customthe resulting solid was removed by celite filtration
  5. distillationThe filtrate was distilled off under reduced pressure
  6. customto remove the solvent
  7. customthe resulting crude product was purified with a silica gel column (ethyl acetate:methanol=15:1 to ethyl acetate:methanol=5:1)
  8. customto obtain the specified substance in the form of a transparent oil at a yield of 0.049 g (yield: 91%)

Sources & evidence

ORD record
ord-a94626e9354046f094a755f1c2717309
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

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