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

HRID 1405964Notes

Reaction equation

[OH:1][C:2]1[C:3]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[C:7]#[N:8].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:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[C:7]#[N:8])[CH2:37][CH2:38][O:39][CH2:40][CH2:41][O:1][C:2]1[C:3]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 5-hydroxy-4-(2-methoxyethoxy)-2-nitrobenzonitrile (0.42 g) in DMF (5 mL) was added 1-bromo-2-(2-(2-(2-bromoethoxy)ethoxy)ethoxy)ethane (0.26 g) and K2CO3 (0.5 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 0.25 g of 5,5′-((((oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))-bis(oxy))bis(4-(2-methoxyethoxy)-2-nitrobenzonitrile). 1H-NMR (400 MHz, CDCl3): δ: 7.84 (s, 2H), 7.35 (s, 2H), 4.33-4.28 (m, 8H), 3.92-3.90 (m, 4H), 3.83-3.81 (m, 4H), 3.73-3.70 (m, 4H), 3.68-3.65 (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-eef205315d9f4798a7dcdeb3978e0f4f
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916572B2

Reaction notes

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