Thionyl Chloride → [Rac]-3-(1-chloro-propyl)-2-methyl-6-(3-trifluoromethyl-phenyl)-pyridine

HRID 1726978Notes

Reaction equation

HRID 1726978 reaction equation
[CH3:1][C:2]1[C:7]([CH:8](O)[CH2:9][CH3:10])=[CH:6][CH:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:3]=1.O=S(Cl)[Cl:24]>C(Cl)Cl>[Cl:24][CH:8]([C:7]1[C:2]([CH3:1])=[N:3][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[CH:5][CH:6]=1)[CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 69039637[Rac]-1-[2-methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-propan-1-ol

Product 1

HCID 21935878[Rac]-3-(1-chloro-propyl)-2-methyl-6-(3-trifluoromethyl-phenyl)-pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.468 g (1.58 mmol) of the above prepared [rac]-1-[2-methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-propan-1-ol was dissolved in 7.6 ml of CH2Cl2 and treated dropwise at 0° C. with 0.23 ml (2 eq.) of SOCl2. The reaction mixture was kept at 0° C. for 5 Min. and at RT for 30 Min. Pouring onto crashed ice/NaHCO3, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents yielded 0.496 g of pure title compound as light yellow oil.

Workup

  1. customwas kept at 0° C. for 5 Min
  2. customat RT
  3. additionPouring
  4. extractionice/NaHCO3, twofold extraction with AcOEt
  5. washwashing with water
  6. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-32409e856f914895b87c233328d81544
Source dataset
uspto-grants-2009_02
Patent number
US07495001B2

Reaction notes

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