Thionyl Chloride → 3-Methoxy-4-ethyl-6-(1-chloroethyl)-pyridine

HRID 1637771Notes

Reaction equation

HRID 1637771 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]([CH:11](O)[CH3:12])=[CH:7][C:8]=1[CH2:9][CH3:10].S(Cl)([Cl:16])=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]([CH:11]([Cl:16])[CH3:12])=[CH:7][C:8]=1[CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 187998333-Methoxy-4-ethyl-6-(1-hydroxyethyl)-pyridine

Product 1

HCID 187997473-Methoxy-4-ethyl-6-(1-chloroethyl)-pyridineYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-methoxy-4-ethyl-6-(1-hydroxyethyl)-pyridine (236 mg, 1.3 mmol) in 5 mL of methylene chloride at 0° C. is treated with thionyl chloride (0.141 mL, 1.95 mmol) and stirred at room temperature for 1 h. The reaction is quenched with 12 mL of saturated sodium bicarbonate. The aqueous layer is extracted with 3×10 mL of methylene chloride. The combined organics are dried over potassium carbonate and concentrated in vacuo to provide 249 mg (96%) of 3-methoxy-4-ethyl-6-(1-chloroethyl)-pyridine.

Workup

  1. customThe reaction is quenched with 12 mL of saturated sodium bicarbonate
  2. extractionThe aqueous layer is extracted with 3×10 mL of methylene chloride
  3. dry with materialThe combined organics are dried over potassium carbonate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5c2a6b3b6103447b9d54e167f14b1f34
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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