Acetonitrile → 3-(3-(2-Ethyl-2-hydroxybutoxy)phenyl)-3-hydroxypropanenitrile

HRID 875511Notes

Reaction equation

HRID 875511 reaction equation
[CH2:1]([C:3]([OH:16])([CH2:14][CH3:15])[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10])[CH3:2].[C:17](#[N:19])[CH3:18]>>[CH2:1]([C:3]([OH:16])([CH2:14][CH3:15])[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:9]([OH:10])[CH2:18][C:17]#[N:19])[CH:11]=[CH:12][CH:13]=1)[CH3:2]

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 866376153-(2-Ethyl-2-hydroxybutoxy)benzaldehyde

Product 1

HCID 673168303-(3-(2-Ethyl-2-hydroxybutoxy)phenyl)-3-hydroxypropanenitrile

Procedure

3-(2-Ethyl-2-hydroxybutoxy)benzaldehyde was reacted with acetonitrile following the method used in Example 13. Purification by flash chromatography (30, 40, 50, 75% EtOAc-hexanes step gradient) gave 3-(3-(2-ethyl-2-hydroxybutoxy)phenyl)-3-hydroxypropanenitrile as an oil. Yield (0.17 g, 79%): 1H NMR (400 MHz, CDCl3) δ 7.23 (t, J=8.0 Hz, 1H), 6.96-6.98 (m, 2H), 6.88-6.91 (m, 1H), 5.02 (t, J=6.4 Hz, 1H), 3.83 (s, 2H), 2.76 (d, J=6.8 Hz, 2H), 1.62-1.68 (m, 4H), 0.92 (t, J=7.6 Hz, 6H).

Workup

  1. customPurification by flash chromatography (30, 40, 50, 75% EtOAc-hexanes step gradient)

Sources & evidence

ORD record
ord-4357b3af06924c4ab6044a834dbff117
Source dataset
uspto-grants-2015_03
Patent number
US08981153B2

Reaction notes

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