Diethyl Ether → 2-Ethyl-6-(((triisopropylsilyl)oxy)methyl)nicotinonitrile

HRID 2247759Notes

Reaction equation

HRID 2247759 reaction equation
CS([C:5]1[N:12]=[C:11]([CH2:13][O:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])[CH:10]=[CH:9][C:6]=1[C:7]#[N:8])(=O)=O.[CH2:25]([Mg]Br)[CH3:26].CCOCC>>[CH2:25]([C:5]1[N:12]=[C:11]([CH2:13][O:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])[CH:10]=[CH:9][C:6]=1[C:7]#[N:8])[CH3:26]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 685269612-(Methylsulfonyl)-6-(((triisopropylsilyl)oxy)methyl)nicotinonitrileHCID 178418443HCID 178418443, compound

Product 1

HCID 685245072-Ethyl-6-(((triisopropylsilyl)oxy)methyl)nicotinonitrile

Procedure

The crude product of the title compound was synthesized by conducting the similar reaction to that mentioned in Example 24 (24c) using 2-(methylsulfonyl)-6-{[(triisopropylsilyl)oxy]methyl}nicotinonitrile (0.78 g, 2.1 mmol) that was obtained in Example 24 (24b) and a 3.0 M solution of ethylmagnesium bromide in ether (1.4 ml, 4.2 mmol). Subsequently, the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (0:10 to 1:9) as the eluent to afford the title compound (0.65 g) in a yield of 97% as a white crystalline solid.

Workup

  1. customthe similar reaction to

Sources & evidence

ORD record
ord-99af06373d2943f291732fbc25d5080e
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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