1,3-Propanediol, 2-methylene- → 2-(2-(Hydroxymethyl)allyloxy)-6-nitrobenzonitrile

HRID 711805Notes

Reaction equation

[N+]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:5]=1[C:6]#[N:7])([O-])=O.[CH2:15]=[C:16]([CH2:19][OH:20])[CH2:17][OH:18]>>[OH:18][CH2:17][C:16](=[CH2:15])[CH2:19][O:20][C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:5]=1[C:6]#[N:7]

Participants

Reactant 2

HCID 770481,3-Propanediol, 2-methylene-

HCID 520718Dinitrobenzonitrile

Product 1

HCID 673992292-(2-(Hydroxymethyl)allyloxy)-6-nitrobenzonitrileYield 55%

Procedure

Prepared as in Example 166d from 2,6-dinitrobenzonitrile and 2-methylenepropane-1,3-diol in 55% yield as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ 7.93 (dd, J=8.4 Hz, J=0.8 Hz, 1H), 7.89 (t, J=8.0 Hz, 1H), 7.73 (dd, J=7.6 Hz, J=0.8 Hz, 1H), 5.23-5.29 (m, 2H), 5.03 (t, J=5.6 Hz, 1H), 4.85 (s, 2H), 4.06 (d, J=5.2 Hz, 2H). |ΠατAππ1009—Λ1|ZZMΠTAΓ|

Sources & evidence

ORD record: ord-9aeab29d9b1a4e1683f905ab087c0b69
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181276B2

Reaction notes

Loading…