Ethanol → 2'-Cyano-5-(methoxycarbonyl)-4'-methylbiphenyl-3-carboxylic acid

HRID 1845195Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1845195
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[C:12]([C:20]([O:22]C)=[O:21])[CH:11]=1)#[N:2].C(O)C.O1CCOCC1.[OH-].[Na+]>O>[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[C:12]([C:20]([OH:22])=[O:21])[CH:11]=1)#[N:2]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 58188054Dimethyl 2'-cyano-4'-methylbiphenyl-3,5-dicarboxylate

Produkt 1

HCID 581883772'-Cyano-5-(methoxycarbonyl)-4'-methylbiphenyl-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A round-bottom flask was charged with dimethyl 2′-cyano-4′-methylbiphenyl-3,5-dicarboxylate (1.5 g, 4.4 mmol), ethanol (100 mL), 1,4-dioxane (20 mL), and a solution of sodium hydroxide (0.17 g, 4.4 mmol) in water (10 mL). The mixture was stirred at room temperature for 3 h. The volatiles were removed under reduced pressure, and the residue was acidified with 1N aq. HCl to pH=4 and extracted with CH2Cl2. The combined organic layers were dried and concentrated. The residue was purified via flash chromatography to afford the desired product 2′-cyano-5-(methoxycarbonyl)-4′-methylbiphenyl-3-carboxylic acid as a white solid. 1H NMR (400 MHz, DMSO-d6): 13.58 (br, 1H), 8.56 (t, J=1.3 Hz, 1H), 8.34-8.31 (m, 2H), 7.85 (s, 1H), 7.65 (d, J=2.6 Hz, 2H), 3.92 (s, 3H), 2.42 (s, 3H). 3-Ethyl 5-methyl 2′-cyano-4′-methylbiphenyl-3,5-dicarboxylate was also isolated as a white solid.

Aufarbeitung

  1. customThe volatiles were removed under reduced pressure
  2. extractionextracted with CH2Cl2
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. customThe residue was purified via flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d0c9f134de18464aaa9cdd9750eeb8d9
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946439B2

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