4-Toluenesulfonyl chloride → HCID 58216658, compound

HRID 1799558Notes

Reaction equation

HRID 1799558 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8]O)[C:5]([C:10]([OH:13])([CH3:12])[CH3:11])=[CH:4][CH:3]=1.C([Li])CCC.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]2[CH2:8][O:13][C:10]([CH3:11])([CH3:12])[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 58216626HCID 58216626, compoundHCID 178418339Butyllithium

Product 1

HCID 58216658HCID 58216658, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[6-Chloro-2-(hydroxymethyl)pyridin-3-yl]propan-2-ol (200 mg, 0.99 mmol) was taken up in tetrahydrofuran (5 mL) and cooled to −78° C. n-Butyllithium (1.24 mL 011.6 M in hexanes, 1.98 mmol) was added dropwise and the mixture was allowed to stir for 30 minutes. p-Toluenesulfonylchloride (190 mg, 0.99 mmol) was then added in one portion and the mixture was allowed to warm to room temperature warm slowly to 0° C. over two hours and then left to warm to room temperature overnight. The reaction was quenched with saturated aqueous ammonium chloride and the biphasic mixture was extracted with ethyl acetate (2×). The combined organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting residue was purified via flash chromatography (silica, 0-50% ethyl acetate/hexanes) to afford the title compound as a colorless oil.

Workup

  1. additionwas added dropwise
  2. temperaturewarm slowly to 0° C. over two hours
  3. waitleft
  4. temperatureto warm to room temperature overnight
  5. customThe reaction was quenched with saturated aqueous ammonium chloride
  6. extractionthe biphasic mixture was extracted with ethyl acetate (2×)
  7. dry with materialThe combined organics were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe resulting residue was purified via flash chromatography (silica, 0-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-516a100354e145f49b21fd20d481f292
Source dataset
uspto-grants-2013_01
Patent number
US08344144B2

Reaction notes

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