4-(Dimethyl-tert-butylsilyl)oxybutan-1-ol → 2-(4-(Tert-butyldimethylsilyloxy)butoxy)-6-nitrobenzonitrile

HRID 471726

Reaction equation

HRID 471726 reaction equation
[C:1]([Si:5]([CH3:13])([CH3:12])[O:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11])([CH3:4])([CH3:3])[CH3:2].[N+:14]([C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([N+]([O-])=O)[C:18]=1[C:19]#[N:20])([O-:16])=[O:15]>>[Si:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:21]1[CH:22]=[CH:23][CH:24]=[C:17]([N+:14]([O-:16])=[O:15])[C:18]=1[C:19]#[N:20])([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 1864034-(Dimethyl-tert-butylsilyl)oxybutan-1-olHCID 520718Dinitrobenzonitrile

Product 1

HCID 667470432-(4-(Tert-butyldimethylsilyloxy)butoxy)-6-nitrobenzonitrileYield 25%

Procedure

Prepared as in Example 215c from 4-(tert-butyldimethyl-silyloxy)butan-1-ol and 2,6-dinitrobenzonitrile in 25% yield as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 0.01 (s, 6H), 0.81-0.83 (m, 9H), 1.61-1.66 (m, 2H), 1.76-1.81 (m, 2H), 3.63 (t, J=6.8 Hz, 2H), 4.26 (t, J=6.4 Hz, 2H), 7.68-7.70 (m, 1H), 7.84-7.89 (m, 2H).

Sources & evidence

ORD record
ord-0d4f0343312448b29bcb534ebe11d334
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Linked notes

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