Sulfuric Acid → 5-(Hydroxy-pyridin-2-yl-methyl)-4'-methyl-biphenyl-3-carboxylic acid

HRID 1845271노트

반응식

HRID 1845271 반응식
[OH:1][CH:2]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)[C:3]1[CH:4]=[C:5]([C:16]([O:18]CC)=[O:17])[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:8]=1.[OH-].[Li+].OS(O)(=O)=O>O1CCOCC1.O>[OH:1][CH:2]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)[C:3]1[CH:4]=[C:5]([C:16]([OH:18])=[O:17])[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:8]=1

참가 물질

6

반응물 3

HCID 1118Sulfuric AcidHCID 3939Lithium HydroxideHCID 58188330Ethyl 5-(hydroxy(pyridin-2-yl)methyl)-4'-methylbiphenyl-3-carboxylate

생성물 1

HCID 581883005-(Hydroxy-pyridin-2-yl-methyl)-4'-methyl-biphenyl-3-carboxylic acid

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

Ethyl 5-(hydroxy(pyridin-2-yl)methyl)-4′-methylbiphenyl-3-carboxylate (319 mg, 0.92 mmol) was dissolved in 1,4-dioxane (6 mL) and water (0.3 mL). To the stirred solution was added lithium hydroxide (120 mg, 5.0 mmol) and the reaction mixture was stirred at room temperature until the reaction was complete. The mixture was cooled and acidified with 2N aq. H2SO4 to pH 5-6 and extracted with EtOAc (20 mL×3). The combined organic layers were washed with brine, dried (MgSO4), and concentrated to yield a light yellow solid. 1H NMR (400 MHz, CD3OD): 8.47 (m, 1H), 8.13 (t, 1H, J=1.6 Hz), 8.02 (t, 1H, J=1.6 Hz), 7.91 (t, 1H, J=1.6 Hz), 7.87 (td, 1H, J=7.6, 1.6 Hz), 7.71 (d, 1H, J=8.0 Hz), 7.51 (d, 2H, J=8.0 Hz), 7.31 (ddd, 1H, J=7.6, 5.2, 1.2 Hz), 7.27 (d, 2H, J=8.0 Hz), 5.93 (s, 1H), 2.37 (s, 3H).

후처리

  1. temperatureThe mixture was cooled
  2. extractionextracted with EtOAc (20 mL×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto yield a light yellow solid

출처 및 근거

ORD 기록
ord-0598d9317c4d4db8b421a98b08097892
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946439B2

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