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

HRID 640401

Reaction equation

HRID 640401 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 carbon tetrachloride (10 mL) solution of (5-benzyloxy-pyridin-2-yl)-methanol (500 mg) described in Manufacturing Example 127-1-2 was added triphenylphosphine (791 mg), which was refluxed for 19 hours and 35 minutes under nitrogen atmosphere. The reaction mixture was cooled to room temperature and then concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=3:1) to obtain the title compound (386 mg).

Workup

  1. temperaturewas refluxed for 19 hours and 35 minutes under nitrogen atmosphere
  2. concentrationconcentrated under a reduced pressure
  3. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-8de60b2a838444a0ba01ab62888a4319
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Linked notes

Loading…