Ethyl Acetate → 4-(2-(2-(2-(2-(5-Cyano-2-(2-methoxyethoxy)-4-nitrophenoxy)ethoxy)ethoxy)ethoxy)ethoxy)-5-(2-methoxyethoxy)-2-nitrobenzonitrile

HRID 1405967Notes

Reaction equation

HRID 1405967 reaction equation
Br[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][C:14]1[C:15]([O:25][CH2:26][CH2:27][O:28][CH3:29])=[CH:16][C:17]([N+:22]([O-:24])=[O:23])=[C:18]([CH:21]=1)[C:19]#[N:20].[OH:30][C:31]1[C:38]([O:39][CH2:40][CH2:41][O:42][CH3:43])=[CH:37][C:34]([C:35]#[N:36])=[C:33]([N+:44]([O-:46])=[O:45])[CH:32]=1.C([O-])([O-])=O.[K+].[K+].CC(=O)OCC>CN(C=O)C.O>[C:19]([C:18]1[C:17]([N+:22]([O-:24])=[O:23])=[CH:16][C:15]([O:25][CH2:26][CH2:27][O:28][CH3:29])=[C:14]([CH:21]=1)[O:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][O:30][C:31]1[C:38]([O:39][CH2:40][CH2:41][O:42][CH3:43])=[CH:37][C:34]([C:35]#[N:36])=[C:33]([N+:44]([O-:46])=[O:45])[CH:32]=1)#[N:20]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 867011884-Hydroxy-5-(2-methoxyethoxy)-2-nitrobenzonitrileHCID 867011955-(2-(2-(2-(2-Bromoethoxy)ethoxy)ethoxy)ethoxy)-4-(2-methoxyethoxy)-2-nitrobenzonitrile

Product 1

HCID 867011944-(2-(2-(2-(2-(5-Cyano-2-(2-methoxyethoxy)-4-nitrophenoxy)ethoxy)ethoxy)ethoxy)ethoxy)-5-(2-methoxyethoxy)-2-nitrobenzonitrileYield 75.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-(2-(2-(2-(2-bromoethoxy)ethoxy)ethoxy)ethoxy)-4-(2-methoxyethoxy)-2-nitrobenzonitrile (0.2 g) in DMF (8 mL) was added 4-hydroxy-5-(2-methoxyethoxy)-2-nitrobenzonitrile (0.1 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 0.2 g of 4-(2-(2-(2-(2-(5-cyano-2-(2-methoxyethoxy)-4-nitrophenoxy)ethoxy)ethoxy)ethoxy)ethoxy)-5-(2-methoxyethoxy)-2-nitrobenzonitrile. 1H-NMR (400 MHz, CDCl3): δ: 7.92 (s, 1H), 7.84 (s, 1H), 7.35 (s, 1H), 7.26 (s, 1H), 4.35-4.25 (m, 8H), 3.95-3.89 (m, 4H), 3.85-3.78 (m, 4H), 3.77-3.63 (m, 8H), 3.45 (s, 6H).

Workup

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

Sources & evidence

ORD record
ord-ae1481724121420c80b067dddd57da92
Source dataset
uspto-grants-2014_12
Patent number
US08916572B2

Reaction notes

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