Prenderol → 2-(2-Ethyl-2-(hydroxymethyl)butoxy)-6-nitrobenzonitrile

HRID 711854Notes

Reaction equation

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

Participants

Reactant 2

HCID 8284Prenderol

HCID 520718Dinitrobenzonitrile

Product 1

HCID 673998802-(2-Ethyl-2-(hydroxymethyl)butoxy)-6-nitrobenzonitrileYield 86%

Procedure

Prepared as in Example 215c from 2,2-diethylpropane-1,3-diol and 2,6-dinitrobenzonitrile in 86% yield. 1H NMR (400 MHz, DMSO-d6) δ 0.80 (t, J=7.6 Hz, 6H), 1.34 (q, J=7.6 Hz, 4H), 3.33 (d, J=5.6 Hz, 2H), 3.96 (s, 2H), 4.57 (t, J=5.2 Hz, 1H), 7.74-7.76 (m, 1H), 7.84-7.90 (m, 2H).

Sources & evidence

ORD record: ord-1f542d92e24846078f0369ae3e4ab501
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181276B2

Reaction notes

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