Diethyl Ether → 2-Chloromethyl-4-ethoxy-5-methylpyridine hydrochloride

HRID 979874Notes

Reaction equation

HRID 979874 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([CH3:10])=[CH:8][N:7]=[C:6]([CH2:11]O)[CH:5]=1)[CH3:2].S(Cl)([Cl:15])=O.CCOCC>C(Cl)Cl>[ClH:15].[Cl:15][CH2:11][C:6]1[CH:5]=[C:4]([O:3][CH2:1][CH3:2])[C:9]([CH3:10])=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 221514614-Ethoxy-5-methyl-2-pyridylmethanol

Product 1

HCID 221514622-Chloromethyl-4-ethoxy-5-methylpyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4.7 g of 4-ethoxy-5-methyl-2-pyridylmethanol, dissolved in 30 ml of methylene chloride, were added dropwise at 0° to 2.4 ml of thionyl chloride in 60 ml of methylene chloride. After stirring at room temperature for 16 hours 400 ml of ether were added dropwise thereto while cooling and the mixture was stirred at room temperature for a further 2 hours. The separated crystals were filtered off under suction and washed with ether. There was obtained 2-chloromethyl-4-ethoxy-5-methylpyridine hydrochloride of melting point 144°-146°.

Workup

  1. additionwere added dropwise
  2. temperaturewhile cooling
  3. filtrationThe separated crystals were filtered off under suction
  4. washwashed with ether

Sources & evidence

ORD record
ord-eca76a19058440cea6c217ed0c513f44
Source dataset
uspto-grants-1987_01
Patent number
US04634710

Reaction notes

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