Pyridine → HCID 22323647, compound

HRID 411854Notes

Reaction equation

HRID 411854 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 mmol) was added CH3CN (200 mL), p-toluenesulfonyl chloride (17 g, 90 mmol) and pyridine (7.3 mL, 90 mmol). The reaction mixture was stirred at room temperature for 12 hours under an atmosphere of argon. Saturated NaHCO3 (200 mL, aq) was added and stirring was continued for 15 minutes. The mixture was then poured into a separatory funnel and extracted several times with CH2Cl2. The CH2Cl2 extracts were combined and dried over Na2SO4. The CH2Cl2 layer was filtered and concentrated in vacuo to give 12.35 g (83.8%) of the title compound. TLC (Rf: 0.5; 20% EtOAc/Hexane). 1H NMR (CDCl3) δ2.1 (m, 2H, CH2), 2.5 (s, 3H, CH3), 3.6 (t, 2H, CH2), 4.2 (t, 2H, CH2), 7.6 (d & d, 4H, Ar). 13C NMR (CDCl3) δ21.4 (CH3), 31.5 (CH2), 40.2 (CH2), 66.7 (CH2), 127.8 (Ar), 129.8 (Ar), 132.5 (Ar), 144.9 (Ar).

Workup

  1. stirringstirring
  2. waitwas continued for 15 minutes
  3. additionThe mixture was then poured into a separatory funnel
  4. extractionextracted several times with CH2Cl2
  5. dry with materialdried over Na2SO4
  6. filtrationThe CH2Cl2 layer was filtered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e13dcebde9f64fae9f9a2cf91f668806
Source dataset
uspto-grants-2003_05
Patent number
US06559303B1

Reaction notes

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