4-Toluenesulfonyl chloride → HCID 87467096, compound

HRID 2064301Notes

Reaction equation

HRID 2064301 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[CH2:10][CH:11]([OH:13])[CH3:12])[CH:5]=[N:6][CH:7]=1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>N1C=CC=CC=1>[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20]([O:13][CH:11]([CH2:10]/[CH:9]=[CH:8]/[C:4]2[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[CH3:12])(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 22060186HCID 22060186, compound

Product 1

HCID 87467096HCID 87467096, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirring solution of (4E)-5-(5-bromo-3-pyridyl)-4-penten-2-ol (3.14 g, 13.0 mmol) in dry pyridine (30 mL) at 0° C. was added p-toluenesulfonyl chloride (3.71 g, 19.5 mmol). The reaction mixture was stirred for 24 h at ambient temperature. The pyridine was removed by rotary evaporation. Toluene (50 mL) was added to the residue and subsequently removed by rotary evaporation. The crude product was stirred with a saturated solution of sodium bicarbonate (100 mL) and extracted with chloroform (3×100 mL). The combined chloroform extracts were dried over sodium sulfate, filtered, and concentrated by rotary evaporation to give (4E)-5-(5-bromo-3-pyridyl)-4-penten-2-ol p-toluenesulfonate. The resulting tosylate was treated with excess methylamine (40% solution in water), ethyl alcohol (10 mL), and stirred at ambient temperature for 18 h. The resulting solution was extracted with chloroform (3×100 mL). The combined chloroform extracts were dried over sodium sulfate and filtered. Removal of solvent by rotary evaporation followed by column chromatography over silica gel eluting with chloroform-methanol (95:5, v/v) produced 1.50 g (45.0%) of a pale-yellow oil.

Workup

  1. customThe pyridine was removed by rotary evaporation
  2. additionToluene (50 mL) was added to the residue
  3. customsubsequently removed by rotary evaporation
  4. stirringThe crude product was stirred with a saturated solution of sodium bicarbonate (100 mL)
  5. extractionextracted with chloroform (3×100 mL)
  6. dry with materialThe combined chloroform extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-d7d3e6c948494c55a80c8faebef40654
Source dataset
uspto-grants-2012_10
Patent number
US08288420B2

Reaction notes

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