Methacrylonitrile → HCID 57936220, compound

HRID 1435057Notes

Reaction equation

HRID 1435057 reaction equation
Cl[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[C:11]1[CH:16]=[CH:15][N:14]=[C:13]([NH:17][CH:18]2[CH2:23][C:22]([CH3:25])([CH3:24])[NH:21][C:20]([CH3:27])([CH3:26])[CH2:19]2)[N:12]=1.[CH3:28][C:29](=[CH2:32])[C:30]#[N:31].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[CH3:32]/[C:29](=[CH:28]\[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[C:11]1[CH:16]=[CH:15][N:14]=[C:13]([NH:17][CH:18]2[CH2:23][C:22]([CH3:24])([CH3:25])[NH:21][C:20]([CH3:27])([CH3:26])[CH2:19]2)[N:12]=1)/[C:30]#[N:31]

Participants

4

Reactant 3

HCID 31368MethacrylonitrileHCID 2724141Tetrabutylammonium FluorideHCID 57936350HCID 57936350, compound

Product 1

HCID 57936220HCID 57936220, compound

Procedure

The title compound was prepared by the general Heck procedure described in Example 256, using the SEM-protected intermediate of Example 228 and 2-methyl-acrylonitrile, followed by TBAF deprotection of the SEM group. The formation of about 20% of the (Z)-Isomer was also observed.

Sources & evidence

ORD record
ord-b1f56d2e11d64c80a235518e0b3f1293
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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