Carbon Tetrachloride → 5-(Benzyloxy)-2-(chloromethyl)pyridine

HRID 1927263Notes

Reaction equation

HRID 1927263 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15]O)=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:37]>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][Cl:37])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 11736050(5-(Benzyloxy)pyridin-2-yl)methanol

Product 1

HCID 178541585-(Benzyloxy)-2-(chloromethyl)pyridine

Procedure

To a solution of carbon tetrachloride (10 mL) of a known compound (5-benzyloxy-pyridin-2-yl)-methanol (500 mg) was added triphenylphosphine (791 mg) at room temperature, which was heated to reflux for 19 hours and 35 minutes under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, after which the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=3:1) to obtain the titled compound (386 mg).

Workup

  1. temperaturewhich was heated
  2. temperatureto reflux for 19 hours and 35 minutes under a nitrogen atmosphere
  3. customafter which the solvent was evaporated under a reduced pressure
  4. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-184e7f8305af4f6ba5128d3214c7811b
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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