Water → 3,4-Bis(phenylthio)-2,5-di(2-thienyl)-tetrahydrofuran

HRID 1955436Notes

Reaction equation

HRID 1955436 reaction equation
[C:1]1([S:7][CH:8]([CH:16]([S:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:17]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)O)[CH:9]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.O>O1CCOCC1>[C:25]1([S:24][CH:16]2[CH:8]([S:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:9]([C:11]3[S:12][CH:13]=[CH:14][CH:15]=3)[O:10][CH:17]2[C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 212617322,3-Bis(phenylthio)-1,4-di(2-thienyl)-1,4-butanediol

Product 1

HCID 110594533,4-Bis(phenylthio)-2,5-di(2-thienyl)-tetrahydrofuran

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 2,3-bis(phenylthio)-1,4-di(2-thienyl)-1,4-butanediol (54.0 g, 114.9 mmol) in 350 ml dioxane there is added 8.70 g conc. sulfuric acid in 4 almost equal portions with a 45 minutes interval between each addition. The rather thick suspension is stirred mechanically for 4 days at room temperature whereby a clear solution is obtained. The solution is poured into 500 ml water and the product is extracted with 2×300 ml toluene. The organic layer is washed with 2×250 ml water, then dried and rotary evaporated. A quantity of 50 ml ether, followed by 200 ml methanol as well as some seed crystals are stirred into the residue. The crystallized product is filtered off and washed with methanol. It weighs 21.83 g. The filtrate is rotary evaporated and the residue is chromatographed on an aluminum oxide column (16×3 cm) using a 1/1 mixture of toluene and hexane as the eluent, thus obtaining a fraction with an additional amount of the product. This fraction is rotary evaporated and the residue is dissolved in some ether. Methanol is added while stirring, whereupon 3,4-bis (phenylthio)-2,5-di(2-thienyl)-tetrahydrofuran crystallizes. It is isolated in the usual way and weighs 7.04 g. The total yield is 28.87 g (63.9 mmol, 56%).

Workup

  1. additionbetween each addition
  2. customis obtained
  3. extractionthe product is extracted with 2×300 ml toluene
  4. washThe organic layer is washed with 2×250 ml water
  5. customdried
  6. stirringare stirred into the residue
  7. filtrationThe crystallized product is filtered off
  8. washwashed with methanol
  9. customThe filtrate is rotary evaporated
  10. customthe residue is chromatographed on an aluminum oxide column (16×3 cm)
  11. additiona 1/1 mixture of toluene and hexane as the eluent
  12. customthus obtaining a fraction with an additional amount of the product
  13. customThis fraction is rotary evaporated
  14. dissolutionthe residue is dissolved in some ether
  15. additionMethanol is added
  16. stirringwhile stirring, whereupon 3,4-bis (phenylthio)-2,5-di(2-thienyl)-tetrahydrofuran
  17. customcrystallizes
  18. customIt is isolated in the usual way

Sources & evidence

ORD record
ord-fcd374e9a35641d392937166a8a4cbf6
Source dataset
uspto-grants-2000_09
Patent number
US06124475

Reaction notes

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