Ammonium Chloride → HCID 19361734, compound

HRID 376291Notes

Reaction equation

HRID 376291 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[O:7]1[CH2:11][CH2:10][O:9][CH:8]1[C:12]1[N:17]=C(C(=O)C)[CH:15]=[CH:14][CH:13]=1.[Cl-].[NH4+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[O:7]1[CH2:11][CH2:10][O:9][CH:8]1[C:12]1[CH:13]=[CH:14][CH:15]=[C:1]([C:2]([CH3:5])=[CH2:3])[N:17]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 10511974HCID 10511974, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19361734HCID 19361734, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

1.62 g of potassium tert-butoxide (14.4 mmol) are added in portions to a suspension of 5.25 g of (methyl)triphenylphosphonium bromide (14.7 mmol) in 30 ml of tetrahydrofuran maintained under a nitrogen atmosphere. The mixture is stirred for 45 minutes and then a solution of 0.95 g of 1-(6-[1,3]dioxolan-2-yl-pyridin-2-yl)ethanone (4.92 mmol) in 5 ml of tetra-hydrofuran is introduced dropwise. The mixture is stirred for 12 hours at room temperature and then it is poured into a saturated aqueous solution of ammonium chloride. The mixture is extracted with ethyl acetate, the organic phase is washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue is taken up in diethyl ether and the precipitate formed is removed by filtration. After evaporation of the solvent, the title product is isolated by chromatography on a silica column (eluent: hexane/ethyl acetate; 85:15). 0.67 g of a pale yellow oil is obtained.

Workup

  1. temperaturemaintained under a nitrogen atmosphere
  2. stirringThe mixture is stirred for 12 hours at room temperature
  3. extractionThe mixture is extracted with ethyl acetate
  4. washthe organic phase is washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customthe precipitate formed
  9. customis removed by filtration
  10. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-ad2aa0fb64ac4db1ae22efc85b881c8d
Source dataset
uspto-grants-2000_02
Patent number
US06020345

Reaction notes

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