4-Toluenesulfonyl chloride → HCID 18920422, compound

HRID 1289139Notes

Reaction equation

HRID 1289139 reaction equation
[OH:1][CH2:2][CH2:3][C:4]#[C:5][C:6]1[S:10][C:9]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:7]=1.[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([Cl:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1>N1C=CC=CC=1>[S:23]([O:1][CH2:2][CH2:3][C:4]#[C:5][C:6]1[S:10][C:9]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:7]=1)([C:20]1[CH:21]=[CH:22][C:17]([CH3:16])=[CH:18][CH:19]=1)(=[O:25])=[O:24].[Cl:26][CH2:2][CH2:3][C:4]#[C:5][C:6]1[S:10][C:9]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 4403573-Butyn-1-ol, 4-(5-(2-thienyl)-2-thienyl)-

Product 2

HCID 18920422HCID 18920422, compoundHCID 18920450HCID 18920450, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

8.48 g of 5-(4-hydroxy-1-butynyl)-2,2'-bithiophene was dissolved in 100 ml of pyridine. 16 g of p-tosyl chloride was added in under nitrogen gas atmosphere. After stirred overnight, the pyridine was evaporated under reduced pressure. The reside was extracted with ethyl acetate (100 ml) twice, filtered, washed with water (100 ml) twice, HCl solution twice (5%, 100 ml) and water (100 ml) twice again. The organic layer dried over anhydrous magnesium sulfate was filtered and the solvent thereof was evaporated. The residual solid was further purified by rapid silica gel column chromatography. From the eluate of ethyl acetate/n-hexane (1/6). 6.25 g of 5-(4-tosyloxy-1-butynyl)-2,2'-bithiophene and 1.48 g of 5-(4-chloro-1-butynyl)-2,2'-bithiophene were respectively obtained and the yield thereof was 44% and 16%.

Workup

  1. customthe pyridine was evaporated under reduced pressure
  2. extractionThe reside was extracted with ethyl acetate (100 ml) twice
  3. filtrationfiltered
  4. washwashed with water (100 ml) twice
  5. dry with materialThe organic layer dried over anhydrous magnesium sulfate
  6. filtrationwas filtered
  7. customthe solvent thereof was evaporated
  8. customThe residual solid was further purified by rapid silica gel column chromatography

Sources & evidence

ORD record
ord-92d4e7d1ddd44e1886e84ecd390d5cbc
Source dataset
uspto-grants-1998_05
Patent number
US05747525

Reaction notes

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