tert-Butyldimethylsilyl chloride → 2-(3-Tert-butyldimethylsilyloxyphenyl)pyridine

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>>[Si:14]([O:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

Reactant 2

HCID 28928tert-Butyldimethylsilyl chloride

HCID 134170943-(Pyridin-2-yl)phenol

Product 1

HCID 497663092-(3-Tert-butyldimethylsilyloxyphenyl)pyridine

Procedure

Then, 2-(3-hydroxyphenyl)pyridine is treated with tert-butyldimethylsilyl chloride (TBDMSCl) to protect the OH group with a tert-butyldimethylsilyl group and give 2-(3-tert-butyldimethylsilyloxyphenyl)pyridine according to scheme (3).

Sources & evidence

ORD record: ord-196847f24e084e8b9a80edf10647037f
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290692B2

Reaction notes

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