4-Toluenesulfonyl chloride → HCID 9179341, compound

HRID 2283270Notes

Reaction equation

HRID 2283270 reaction equation
[OH-].[K+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][OH:10].[S:11](Cl)([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12]>C1COCC1>[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][O:10][S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 11474PiconolHCID 14797Potassium Hydroxide

Product 1

HCID 9179341HCID 9179341, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Powdered KOH (1.74 g, 30.65 mmol) was added to a vigorously stirred solution of pyridin-2-yl-methanol (2 mL, 20.72 mmol) in THF (100 mL) at 0° C. The reaction mixture was stirred for 15 minutes and tosyl chloride (5.13 g, 26.90 mmol) was then added. The reaction mixture was allowed to warm to RT and stirring was continued overnight. The reaction mixture was quenched with saturated NaHCO3 and the product was extracted with EtOAc (3×50 mL). The combined extracts were dried over MgSO4 and concentrated in vacuo to give a yellow oil. The residue was purified by flash column chromatography using EtOAc: hexane (1:4) to yield the title compound (4.6 g, 85%) as a yellowish solid.

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. customThe reaction mixture was quenched with saturated NaHCO3
  4. extractionthe product was extracted with EtOAc (3×50 mL)
  5. dry with materialThe combined extracts were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give a yellow oil
  8. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-47a8dc66312d4171a96205f5100e27b3
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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