Lithium Hydroxide → 2'-Cyano-5-(hydroxymethyl)-4'-methylbiphenyl-3-carboxylic acid

HRID 1845302노트

반응식

HRID 1845302 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]([CH2:16][OH:17])[CH:13]=[C:12]([C:18]([O:20]C)=[O:19])[CH:11]=1)#[N:2].[OH-].[Li+].[NH4+].[Cl-].CCOC(C)=O>O1CCOCC1.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]([CH2:16][OH:17])[CH:13]=[C:12]([C:18]([OH:20])=[O:19])[CH:11]=1)#[N:2]

참가 물질

7

반응물 4

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 58187956Methyl 2'-cyano-5-(hydroxymethyl)-4'-methylbiphenyl-3-carboxylate

생성물 1

HCID 581883422'-Cyano-5-(hydroxymethyl)-4'-methylbiphenyl-3-carboxylic acid

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

To a stirred solution of methyl 2′-cyano-5-(hydroxymethyl)-4′-methylbiphenyl-3-carboxylate (220 mg, 0.78 mmol) in 1,4-dioxane (5 mL) and water (1 mL) was added lithium hydroxide (60 mg, 2.5 mmol). The reaction mixture was stirred at rt for 8 h, and then treated with aq. NH4Cl and EtOAc. The organic layer was separated, dried over anhydrous MgSO4, and concentrated. The residue was purified by silica gel chromatography to afford the title compound. 1H NMR (acetone-d6, 400 MHz): 8.16 (m, 1H), 8.11 (m, 1H), 7.81 (m, 1H), 7.73 (m, 1H), 7.65-7.61 (m, 1H), 7.56 (d, 1H, J=8.0 Hz), 4.81 (s, 2H), 2.46 (s, 3H).

후처리

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-05c5e1b0124749b193f10313bf558961
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946439B2

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