3,4-Bis(diethoxyphosphoryl)-2,3-dihydrothiophene → HCID 59155862, compound

HRID 1662862Notes

Reaction equation

HRID 1662862 reaction equation
[CH2:1]([O:3][P:4]([CH:9]1[C:13]([P:14]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][S:11][CH2:10]1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]>C1C=CC=CC=1.[O-2].[Mn+4].[O-2]>[CH2:17]([O:16][P:14]([C:13]1[C:9]([P:4]([O:3][CH2:1][CH3:2])([O:6][CH2:7][CH3:8])=[O:5])=[CH:10][S:11][CH:12]=1)([O:19][CH2:20][CH3:21])=[O:15])[CH3:18]

Participants

4

Reactant 1

HCID 866384053,4-Bis(diethoxyphosphoryl)-2,3-dihydrothiophene

Product 1

HCID 59155862HCID 59155862, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 178418406HCID 178418406, compoundSolvent

Procedure

In benzene, 9.740 g (112 mmols) of commercially available manganese (IV) oxide was dissolved, to which 2.010 g (5.60 mmols) of 3,4-bis(diethoxyphosphoryl)-2,3-dihydrothiophene was added at room temperature. Thereafter, the reaction mixture was heated and stirred under reflux for 29 hours. After the reaction, the reaction mixture was cooled down to room temperature and the 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 obtain the specified substance in the form of a brown solid at a yield of 1.700 g (yield: 85.4%).

Workup

  1. additionwas added at room temperature
  2. temperatureThereafter, the reaction mixture was heated
  3. temperatureunder reflux for 29 hours
  4. customAfter the reaction
  5. customthe solid was removed by celite filtration
  6. distillationThe filtrate was distilled off under reduced pressure
  7. customto remove the solvent
  8. customthe resulting crude product was purified with a silica gel column (ethyl acetate:methanol=15:1)
  9. customto obtain the specified substance in the form of a brown solid at a yield of 1.700 g (yield: 85.4%)

Sources & evidence

ORD record
ord-46aca065eab84388a9c1436e80c8af96
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

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