Water → 4,4'-((((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))-bis(oxy))bis(5-(2-methoxyethoxy)-2-nitrobenzonitrile)

HRID 1405959Notes

Reaction equation

[OH:1][C:2]1[C:9]([O:10][CH2:11][CH2:12][O:13][CH3:14])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N+:15]([O-:17])=[O:16])[CH:3]=1.Br[CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29]Br.[C:31]([O-:34])([O-])=O.[K+].[K+].[CH3:37][C:38](=O)[O:39][CH2:40][CH3:41].[OH2:43]>CN(C=O)C>[O:43]([CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][C:25]1[C:26]([O:27][CH2:28][CH2:29][O:34][CH3:31])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N+:15]([O-:17])=[O:16])[CH:3]=1)[CH2:37][CH2:38][O:39][CH2:40][CH2:41][O:1][C:2]1[C:9]([O:10][CH2:11][CH2:12][O:13][CH3:14])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N+:15]([O-:17])=[O:16])[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-hydroxy-5-(2-methoxyethoxy)-2-nitrobenzonitrile. (0.25 g) in DMF (5 mL) was added 1-bromo-2-(2-(2-(2-bromoethoxy) ethoxy)ethoxy)ethane (0.15 g) and K2CO3 (0.3 g). The resulting mixture was heated at 80° C. overnight under N2 atmospheres. After reaction finished, the mixture was diluted with water (50 mL) and exacted with EA (3×50 mL). The combined organic layer was dried over Na2SO4, concentrated under reduced pressure, and purification by silica chromatography to give 0.3 g 4,4′-((((oxybis(ethane-2,1-diyl))-bis(oxy))bis(ethane-2,1-diyl))-bis(oxy))bis-(5-(2-methoxyethoxy)-2-nitrobenzonitrile). 1H-NMR (400 MHz, CDCl3): δ: 7.92 (s, 2H), 7.26 (s, 2H), 4.36-4.27 (m, 8H), 3.92-3.90 (m, 4H), 3.83-3.81 (m, 4H), 3.70-3.69 (m, 4H), 3.65-3.63 (m, 4H), 3.45 (s, 6H).

Workup

customAfter reaction
dry with materialThe combined organic layer was dried over Na2SO4
concentrationconcentrated under reduced pressure, and purification by silica chromatography

Sources & evidence

ORD record: ord-3c231f6aaa714b33b5a77d8876cf42e4
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916572B2

Reaction notes

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