2-ethynylbenzonitrile → 2-[6-(Trimethylsilyl)hex-3-ene-1,5-diyn-1-yl]benzonitrile

HRID 2055839Notes

Reaction equation

HRID 2055839 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[C:3]#[C:4][CH:5]=[CH:6]Cl.[C:10]([C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15])#[CH:11]>>[CH3:1][Si:2]([CH3:9])([CH3:8])[C:3]#[C:4][CH:5]=[CH:6][C:11]#[C:10][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15]

Participants

3

Reactant 2

HCID 111160742-ethynylbenzonitrile2×HCID 53822143(4-Chlorobut-3-en-1-yn-1-yl)(trimethyl)silane2×

Product 1

HCID 713745812-[6-(Trimethylsilyl)hex-3-ene-1,5-diyn-1-yl]benzonitrileYield 53%

Procedure

The Title compound may be produced in two steps using compound a1 Example 1 and compound a3 from Example 3 as starting materials. Firstly, compound a1 and compound a3 were reacted according to Method A set forth in the above-described General Synthesis Procedures I to form 2-(6-trimethylsilyl-3-hexen-1,5-diynyl)benzonitrile, which was subsequently dissolved into into dry methanol with K2CO3 to give a brown oil in 53% yield.

Workup

  1. customaccording to Method A set forth in the above-described General Synthesis Procedures I

Sources & evidence

ORD record
ord-6d359e3b2e90493e976c4074d61abfef
Source dataset
uspto-grants-2008_02
Patent number
US07332623B2

Reaction notes

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