Acetonitrile → HCID 68942150, compound

HRID 242735Notes

Reaction equation

HRID 242735 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:3]=1/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10].[C:19](#[N:21])[CH3:20]>>[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:3]=1/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]([CH:9]([OH:10])[CH2:20][C:19]#[N:21])[CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 86632164HCID 86632164, compound

Product 1

HCID 68942150HCID 68942150, compound

Procedure

(E)-3-(2-Chloro-6-methylstyryl)benzaldehyde was reacted with acetonitrile according to the procedure used in Example 50. Purification by flash chromatography (10 to 70% EtOAc-hexanes gradient) gave (E)-3-(3-(2-chloro-6-methylstyryl)phenyl)-3-hydroxypropanenitrile as an oil. Yield 0.0708 g, 77%): 1H NMR (400 MHz, CDCl3) δ 7.51-7.53 (m, 2H), 7.41 (t, J=8.0 Hz, 1H), 7.25-7.33 (m, 2H), 7.07-7.20 (m, 3H), 6.80 (d, J=16.8 Hz, 1H), 5.08 (t, J=6.4 Hz, 1H), 2.80 (dd, J=6.4, 0.8 Hz, 2H), 2.43 (s, 3H).

Workup

  1. customPurification by flash chromatography (10 to 70% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-c3d14fe33ddd498789e5dee3abff54cb
Source dataset
uspto-grants-2014_02
Patent number
US08653142B2

Reaction notes

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