Thionyl Chloride → 2-Chloro-3-methoxy-4-vinyl-6-(1-chloroethyl)-pyridine

HRID 1637769Notes

Reaction equation

HRID 1637769 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([CH:10]=[CH2:11])[CH:5]=[C:4]([CH:12](O)[CH3:13])[N:3]=1.S(Cl)([Cl:17])=O>C(Cl)Cl>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([CH:10]=[CH2:11])[CH:5]=[C:4]([CH:12]([Cl:17])[CH3:13])[N:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 18799939HCID 18799939, compound

Product 1

HCID 187997872-Chloro-3-methoxy-4-vinyl-6-(1-chloroethyl)-pyridineYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-chloro-3-methoxy-4-vinyl-6-(1-hydroxyethyl)-pyridine (446 mg, 2.09 mmol) in 10 mL of methylene chloride at 0° C. is treated with thionyl chloride (0.227 mL, 3.13 mmol) and stirred at room temperature for 1 h. The reaction is quenched with 15 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 447 mg (92%) of 2-chloro-3-methoxy-4-vinyl-6-(1-chloroethyl)-pyridine.

Workup

  1. customThe reaction is quenched with 15 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-1d551c35b1cc4323b8710edd95fbe3ac
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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