Pyridine → HCID 12634867, compound

HRID 914470Notes

Reaction equation

HRID 914470 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH2:10]O)=[CH:4][CH:3]=1.N1C=CC=CC=1.S(Cl)([Cl:20])=O>ClCCl>[Cl:20][CH2:10]/[CH:9]=[CH:8]/[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 13371325HCID 13371325, compound

Product 1

HCID 12634867HCID 12634867, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(2E)-3-(4-Fluorophenyl)prop-2-en-1-ol (1.36 g) synthesized in Reference Example 24 was dissolved in dichloromethane (45 mL), pyridine (0.78 g) and thionyl chloride (0.72 mL) were added under ice-cooling, and the mixture was stirred for 30 min. The mixture was diluted with dichloromethane. The organic layer was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane) to give the title compound (1.1 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. washThe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (elution solvent; hexane)

Sources & evidence

ORD record
ord-230c2dbdac8b4f96af1b6990a6392d4e
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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