HCID 86638407, compound → HCID 86638409, compound

HRID 1662868Notes

Reaction equation

HRID 1662868 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 38%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

In THF, 0.082 g (0.171 mmols) of the 2-iodo-3,4-bis(diethoxyphosphoryl)thiophene obtained in Example 4 and 0.009 g (0.00775 mmols) of commercially available tetrakistriphenylphosphine palladium, and 0.0014 g (0.0155 mmols) of commercially available copper(I) chloride were dissolved, to which 0.100 g (0.155 mmols) of the 2-tributylstannyl-3,4-bis(diethoxyphosphoryl)thiophene obtained in Example 5 was added at room temperature. Thereafter, the reaction mixture was heated to 70° C. and stirred for 11 hours. After the reaction, the reaction mixture was cooled down to room temperature, followed by distilling 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 at a yield of 0.046 g (yield: 38%).

Workup

  1. additionwas added at room temperature
  2. customAfter the reaction
  3. temperaturethe reaction mixture was cooled down to room temperature
  4. distillationby distilling off under reduced pressure
  5. customto remove the solvent
  6. customthe resulting crude product was purified with a silica gel column (ethyl acetate:methanol=15:1 to ethyl acetate:methanol=5:1)
  7. customto obtain the specified substance at a yield of 0.046 g (yield: 38%)

Sources & evidence

ORD record
ord-394cd61a49f84646a6b7726ac98fc00f
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

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