Lithium diisopropylamide → 3-(3-(2-Ethylbutoxy)phenyl)-3-hydroxypropanenitrile

HRID 875519Notes

Reaction equation

HRID 875519 reaction equation
[CH2:1]([CH:3]([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].[Li+].[CH3:17][CH:18]([N-:20]C(C)C)C>C(#N)C>[CH2:14]([CH:3]([CH2:1][CH3:2])[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:9]([OH:10])[CH2:17][C:18]#[N:20])[CH:11]=[CH:12][CH:13]=1)[CH3:15]

Participants

4

Reactant 2

HCID 2724682Lithium diisopropylamideHCID 829274743-(2-Ethylbutoxy)benzaldehyde

Product 1

HCID 673172123-(3-(2-Ethylbutoxy)phenyl)-3-hydroxypropanenitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Reaction of 3-(2-ethylbutoxy)benzaldehyde with acetonitrile in the presence of LDA gave 3-(3-(2-ethylbutoxy)phenyl)-3-hydroxypropanenitrile. 1H NMR (400 MHz, DMSO-d6) δ 7.22 (t, J=7.2 Hz, 1H), 6.92-6.96 (m, 2H), 6.81-6.83 (m, 1H), 5.89 (brs, 1H), 4.83 (brs, 1H), 3.82 (d, J=6.4 Hz, 2H), 2.73-2.90 (m, 2H), 1.56-1.64 (m, 1H), 1.31-1.44 (m, 4H), 0.87 (t, J=7.6 Hz, 6H).

Sources & evidence

ORD record
ord-5a2a2e9dddea4692bac1b15fa5a5b4ea
Source dataset
uspto-grants-2015_03
Patent number
US08981153B2

Reaction notes

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