Thionyl Chloride → HCID 19783302, compound

HRID 257476Notes

Reaction equation

HRID 257476 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9](O)[CH:10]([C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)[CH3:11].S(Cl)(Cl)=O>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8]/[CH:9]=[C:10](\[C:12]1[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=1)/[CH3:11]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 19783305HCID 19783305, compound

Product 1

HCID 19783302HCID 19783302, compoundYield 36.6%

Conditions

Temperature
40 °C

Procedure

To the said solid, that is, 1.59 g (6.49 mmol) of 1-(2-fluorophenyl)-3-(4-pyridyl)-2-butanol, 2.5 ml of thionyl chloride was added and stirred for one hour at 40° C. After distilling away excessive thionyl chloride under reduced pressure, water was added and the residue was alkalized with sodium carbonate and was extracted with ethyl acetate. After drying over anhydrous sodium sulfate, ethyl acetate was distilled away under reduced pressure to obtain a brown oily substance. The resulting oily substance was purified by silica gel column chromatography to obtain 0.54 g of the desired compound (yield: 31.6%).

Workup

  1. distillationAfter distilling away excessive thionyl chloride under reduced pressure, water
  2. additionwas added
  3. extractionwas extracted with ethyl acetate
  4. dry with materialAfter drying over anhydrous sodium sulfate, ethyl acetate
  5. distillationwas distilled away under reduced pressure
  6. customto obtain a brown oily substance
  7. customThe resulting oily substance was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1d5fe70ccd91474db0ddf7bfd8c7a36f
Source dataset
uspto-grants-1993_11
Patent number
US05262420

Reaction notes

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