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

HRID 1845195노트

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HRID 1845195 반응식
[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]

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6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d0c9f134de18464aaa9cdd9750eeb8d9
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946439B2

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