Tetrahydrofuran → HCID 12766301, compound

HRID 1155513Notes

Reaction equation

HRID 1155513 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]([S:22]C3C=CC([N+]([O-])=O)=CC=3[N+]([O-])=O)=[CH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.O1CCCC1.[OH-].[K+].[F:42][C:43]([F:47])=[C:44]([F:46])[F:45]>CO.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]([S:22][C:44]([F:46])([F:45])[CH:43]([F:47])[F:42])=[CH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8301TetrafluoroethyleneHCID 14797Potassium HydroxideHCID 20561020HCID 20561020, compound

Product 1

HCID 12766301HCID 12766301, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

2,3-bis(4-Methoxyphenyl)-5-(2,4-dinitrophenylthio)thiophene (4.9 g, 10 mmoles), tetrahydrofuran (60 ml), methanol/water (7.5 ml, 2.5 ml) and potassium hydroxide (1.3 g, 20 mmoles) were charged into a stainless steel bomb. The bomb was briefly evacuated, charged with tetrafluoroethylene (5 g, 50 mmoles) and agitated for 12 hours at room temperature. The reaction mixture was filtered and the filtrate concentrated to near dryness. The residue was taken up in ethyl acetate and filtered. The filtrate was washed three times with 1 N NaOH, three times with 1 N HCl, once with brine, dried and concentrated in vacuo. Crystallization from ethanol/water gave the title compound (2.4 g), m.p. 84°-7° (D). Infrared and H-NMR spectra were consistent with the assigned structure. MS 428 (M+)

Workup

  1. customThe bomb was briefly evacuated
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated
  4. filtrationfiltered
  5. washThe filtrate was washed three times with 1 N NaOH, three times with 1 N HCl
  6. dry with materialonce with brine, dried
  7. concentrationconcentrated in vacuo
  8. customCrystallization from ethanol/water

Sources & evidence

ORD record
ord-d275c25a1fd54e38828871feeea60ce7
Source dataset
uspto-grants-1981_11
Patent number
US04302461

Reaction notes

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