Pyridine → HCID 22323647, compound

HRID 1954441Notes

Reaction equation

HRID 1954441 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][OH:5].[C:6]1([CH3:16])[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][CH:7]=1.N1C=CC=CC=1.C([O-])(O)=O.[Na+]>CC#N>[C:6]1([CH3:16])[CH:11]=[CH:10][C:9]([S:12]([CH:4]([OH:5])[CH2:3][CH2:2][Cl:1])(=[O:14])=[O:13])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 123133-Chloro-1-propanolHCID 516892Sodium Bicarbonate

Product 1

HCID 22323647HCID 22323647, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 3-chloro-1-propanol (5.02 mL, 60 mmole) in CH3CN (200 mL) was added, p-toluenesufonyl chloride (17 g, 90 mmole) and pyridine (7.3 mL, 90 mmole). The reaction mixture was stirred at room temperature for 12 hours under an argon atmosphere. 200 mL of saturated NaHCO3 (aq) was added and the stirring was continued for 15 minutes. The mixture was extracted several times with CH2Cl2. The combine CH2Cl2 layers were dried over Na2SO4, the Na2SO4 was filtered and the filtrate was evaporated to give 12.35 g (83.8%) of the title compound: TLC (Rf: 0.5; 20% EtOAc/Hexane), 1H NMR (CDCl3) δ 2.1 (m, 2 H, CH2), 2.5 (s, 3 H, CH3), 3.6 (t, 2 H, CH2), 4.2 (t, 2 H, CH2), 7.6 (d & d, 4 H, Ar). 13C NMR (CDCl3): δ 21.4 (CH3), 31.5 (CH2), 40.2 (CH2), 66.7 (CH2), 127.8 (Ar), 129.8 (Ar), 132.5 (Ar), 144.9 (Ar).

Workup

  1. waitthe stirring was continued for 15 minutes
  2. extractionThe mixture was extracted several times with CH2Cl2
  3. dry with materialThe combine CH2Cl2 layers were dried over Na2SO4
  4. filtrationthe Na2SO4 was filtered
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-7493af49577c4752977af3a2e594e78b
Source dataset
uspto-grants-2000_09
Patent number
US06121433

Reaction notes

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