Hydrogen iodide → HCID 15020365, compound

HRID 1460250Notes

Reaction equation

HRID 1460250 reaction equation
[CH:1]1([C:7]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.I.[P]>C(O)(=O)C>[CH:1]1([CH:7]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 24841Hydrogen iodideHCID 5462309PhosphorusHCID 15020364HCID 15020364, compound

Product 1

HCID 15020365HCID 15020365, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of α-cyclohexyl-α-(4-fluorophenyl)-4-pyridinemethanol (16.54 g, 0.058 mole), 57% hydrogen iodide (250 ml), glacial acetic acid (250 ml), and phosphorus (50.0 g) was heated overnight at reflux. The reaction mixture was cooled and filtered through Celite®. The volume of the filtrate was concentrated to 100 ml. Ice/50% sodium hydroxide was added, and the aqueous phase was extracted with chloroform. The chloroform layer was back extracted with 5% sodium hydroxide and water. The organic layer was dried over sodium sulfate and filtered, and solvent removed to give a green oil. A 4 g portion of this oil was subjected to flash chromatography on silica gel using 20% ethyl acetate-hexanes for elution. Fractions of similar purity were combined and solvent removed to give an oil. This oil was dried in vacuo overnight at 80° C. The oil crystallized to give 2.95 g (19% yield) of white, crystalline solid, mp 78°-81° C.

Workup

  1. temperaturewas heated overnight
  2. temperatureat reflux
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered through Celite®
  5. concentrationThe volume of the filtrate was concentrated to 100 ml
  6. additionIce/50% sodium hydroxide was added
  7. extractionthe aqueous phase was extracted with chloroform
  8. extractionThe chloroform layer was back extracted with 5% sodium hydroxide and water
  9. dry with materialThe organic layer was dried over sodium sulfate
  10. filtrationfiltered
  11. customsolvent removed
  12. customto give a green oil
  13. washA 4 g portion of this oil was subjected to flash chromatography on silica gel using 20% ethyl acetate-hexanes for elution
  14. customsolvent removed
  15. customto give an oil
  16. customThis oil was dried in vacuo overnight at 80° C
  17. customThe oil crystallized
  18. customto give 2.95 g (19% yield) of white, crystalline solid, mp 78°-81° C.

Sources & evidence

ORD record
ord-ceeb8df1a5bf483da6a28b95b0e32bf4
Source dataset
uspto-grants-1991_12
Patent number
US05070087

Reaction notes

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