Acetonitrile → (E)-3-(5-(2-cyclohexylvinyl)pyridin-3-yl)-3-hydroxypropanenitrile

HRID 63307Notes

Reaction equation

HRID 63307 reaction equation
[CH:1]1(/[CH:7]=[CH:8]/[C:9]2[CH:10]=[N:11][CH:12]=[C:13]([CH:16]=2)[CH:14]=[O:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:17][C:18]#[N:19]>>[CH:1]1(/[CH:7]=[CH:8]/[C:9]2[CH:16]=[C:13]([CH:14]([OH:15])[CH2:17][C:18]#[N:19])[CH:12]=[N:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 86694593(E)-5-(2-cyclohexylvinyl)nicotinaldehyde

Product 1

HCID 86694594(E)-3-(5-(2-cyclohexylvinyl)pyridin-3-yl)-3-hydroxypropanenitrile

Procedure

Addition of CH3CN to (E)-5-(2-cyclohexylvinyl)nicotinaldehyde following the method used in Example 3 gave (E)-3-(5-(2-cyclohexylvinyl)pyridin-3-yl)-3-hydroxypropanenitrile as a yellow oil. Yield (0.9 g, 95%); 1H NMR (400 MHz, CDCl3) δ 8.43 (s, 1H), 8.41 (s, 1H), 7.93 (s, 1H), 6.42 (s, 2H), 5.05 (t, J=5.6 Hz, 1H), 2.98-2.82 (m, 2H), 2.24-2.12 (m, 1H), 1.88-1.66 (m, 5H), 1.42-1.18 (m, 5H).

Sources & evidence

ORD record
ord-282fbe10d6ac4d57886277b2ebd78b1a
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Reaction notes

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