Carbon Tetrachloride → 4-(3-Chloropropyl)pyridine

HRID 1458952Notes

Reaction equation

HRID 1458952 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](C(O)CC)[CH:2]=1.[C:11]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:16]=CC=C[CH:12]=1.C(Cl)(Cl)(Cl)[Cl:31]>C1COCC1>[N:1]1[CH:2]=[CH:3][C:4]([CH2:12][CH2:11][CH2:16][Cl:31])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 110839421-(Pyridin-3-yl)propan-1-ol

Product 1

HCID 2054424-(3-Chloropropyl)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-pyridylpropanol (2-2) (ICN Biochemicals, 14.2 g, 0.1 mol) in THF (200 mL) was treated successively with triphenylphosphine (47.2 g, 0.18 mol) and carbontetrachloride (17.4 mL, 0.18 mol) and stirred for 24 h. The reaction was filtered and the solids washed with Et2O. The filtrate was concentrated to give a yellow solid which was triturated with Et2O. Chromatography (silica gel, 30% EtOAc/Hexanes) gave 2-3 as yellow oil.

Workup

  1. filtrationThe reaction was filtered
  2. washthe solids washed with Et2O
  3. concentrationThe filtrate was concentrated
  4. customto give a yellow solid which
  5. customwas triturated with Et2O

Sources & evidence

ORD record
ord-971b659f5de24d80b7911e97c66389be
Source dataset
uspto-grants-1998_12
Patent number
US05852045

Reaction notes

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