Acetonitrile → 3-Hydroxy-3-(3-(2-propylpentyloxy)phenyl)propanenitrile

HRID 875507Notes

Reaction equation

HRID 875507 reaction equation
[CH2:1]([CH:4]([CH2:15][CH2:16][CH3:17])[CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=[O:11])[CH2:2][CH3:3].[C:18](#[N:20])[CH3:19]>>[OH:11][CH:10]([C:9]1[CH:12]=[CH:13][CH:14]=[C:7]([O:6][CH2:5][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:15][CH2:16][CH3:17])[CH:8]=1)[CH2:19][C:18]#[N:20]

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 866376143-(2-Propylpentyloxy)benzaldehyde

Product 1

HCID 673171733-Hydroxy-3-(3-(2-propylpentyloxy)phenyl)propanenitrile

Procedure

Reaction of 3-(2-propylpentyloxy)benzaldehyde with acetonitrile was conducted following the method used for Example 20. Purification by flash chromatography (20% EtOAc-hexanes) gave 3-hydroxy-3-(3-(2-propylpentyloxy)phenyl)propanenitrile as a clear oil. Yield (1.05 g, 59%): 1H NMR (DMSO-d6) δ 7.21 (t, J=8.0 Hz, 1H), 6.92-6.95 (m, 2H), 6.81 (ddd, J=8.0, 2.4, 0.8 Hz, 1H), 5/87 (br s, 1H), 4.82 (t, J=6.4 Hz, 1H), 3.81 (d, J=5.6 Hz, 1H), 2.86 (dd, J=16.8, 5.0 Hz, 1H), 2.77 (dd, J=17.2, 6.8 Hz, 1H), 1.74 (quint., J=5.6 Hz, 1H), 1.26-1.40 (m, 8H), 0.84-0.87 (m, 6H).

Workup

  1. customPurification by flash chromatography (20% EtOAc-hexanes)

Sources & evidence

ORD record
ord-43a37c9ec90b4d5fa03e268a52ab90b3
Source dataset
uspto-grants-2015_03
Patent number
US08981153B2

Reaction notes

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