Thionyl Chloride → HCID 118114064, compound

HRID 2178368Notes

Reaction equation

HRID 2178368 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9](O)[CH2:10][CH3:11])=[CH:5][CH:4]=1.S(Cl)([Cl:15])=O>ClCCl>[Cl:15][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[N:8][CH:7]=1)[CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 102546535HCID 102546535, compound

Product 1

HCID 118114064HCID 118114064, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(6-methoxypyridin-3-yl)propan-1-ol (1.67 g, 9.99 mmol) in dichloromethane (30 mL) at 0° C. was added thionyl chloride (2.46 g, 1.5 mL, 20.68 mmol). The cooling bath was removed, and the mixture was allowed to warm to room temperature. After 1 h, the reaction was quenched by the addition of saturated aqueous sodium bicarbonate solution. The phases were separated, and the organic phase was washed with brine (20 mL), dried over sodium sulfate, filtered, and concentrated to provide 1.50 g (81%) of 5-(1-chloropropyl)-2-methoxypyridine as a yellow oil.

Workup

  1. customThe cooling bath was removed
  2. customthe reaction was quenched by the addition of saturated aqueous sodium bicarbonate solution
  3. customThe phases were separated
  4. washthe organic phase was washed with brine (20 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-07397a86df884e059d469e4adce8aa2c
Source dataset
uspto-grants-2015_06
Patent number
US09067914B1

Reaction notes

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