Acetonitrile → 3-[3-(5-Benzyloxypentoxy)-phenyl]-3-hydroxypropionitrile

HRID 1014667Notes

Reaction equation

HRID 1014667 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](#[N:25])[CH3:24]>>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:18]([OH:19])[CH2:24][C:23]#[N:25])[CH:20]=[CH:21][CH:22]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 866376213-(5-Benzyloxypentoxy)-benzaldehyde

Product 1

HCID 673168573-[3-(5-Benzyloxypentoxy)-phenyl]-3-hydroxypropionitrile

Procedure

Addition of acetonitrile to 3-(5-(benzyloxy)pentyloxy)benzaldehyde gave 3-(3-(5-(benzyloxy)pentyloxy)phenyl)-3-hydroxypropanenitrile as a yellow oil. Yield (0.74 g, 51%): 1H NMR (400 MHz, CDCl3) δ 7.27-7.37 (m, 6H), 6.93-6.96 (m, 2H), 6.86 (d, J=8.0 Hz, 1H), 5.0-5.05 (m, 1H), 4.51 (s, 2H), 3.97 (t, J=6.4 Hz, 2H), 3.51 (t, J=6.4 Hz, 2H), 2.76 (d, J=6.0 Hz, 2H), 2.30 (s, 1H), 1.78-1.85 (m, 2H), 1.58-1.64 (m, 2H), 1.52-1.58 (m, 2H).

Sources & evidence

ORD record
ord-fefecc114a1c4d68a098af30dec2f78c
Source dataset
uspto-grants-2011_07
Patent number
US07982071B2

Reaction notes

Loading…