Carbon Tetrachloride → 2-(4-Chloromethyl-benzyloxy)-pyridine

HRID 1927259Notes

Reaction equation

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

Participants

Reactant 3

HCID 5943Carbon Tetrachloride

HCID 11776Triphenylphosphine

HCID 59255473(4-(Pyridin-2-yloxymethyl)-phenyl)-methanol

Product 1

HCID 592550952-(4-Chloromethyl-benzyloxy)-pyridineYield 51.1%

Procedure

(4-(Pyridin-2-yloxymethyl)-phenyl)methanol (540 mg, 2.51 mmol) described in Manufacturing Example 26-1, triphenylphosphine (856 mg, 3.27 mmol), and carbon tetrachloride (10.8 g, 10.2 mmol) were stirred for 2 hours and 10 minutes under heating and reflux. The reaction solution was cooled to room temperature, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=8:1) to obtain the titled compound (300 mg).

Workup

temperatureunder heating
temperaturereflux
customthe solvent was evaporated under a reduced pressure
customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=8:1)

Sources & evidence

ORD record: ord-8c1d3d5391d6438a89a4f902ccf557de
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183264B2

Reaction notes

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