Lithium Hydroxide → 2'-Cyano-4'-methyl-5-(2,2,2-trifluoro-1-hydroxyethyl)biphenyl-3-carboxylic acid

HRID 1845306ノート

反応式

HRID 1845306 の反応式
[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]([CH:16]([OH:21])[C:17]([F:20])([F:19])[F:18])[CH:13]=[C:12]([C:22]([O:24]C)=[O:23])[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]([CH:16]([OH:21])[C:17]([F:18])([F:20])[F:19])[CH:13]=[C:12]([C:22]([OH:24])=[O:23])[CH:11]=1)#[N:2]

参加物

7

反応物 4

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 58188274Methyl 2'-cyano-4'-methyl-5-(2,2,2-trifluoro-1-hydroxyethyl)biphenyl-3-carboxylate

生成物 1

HCID 581880842'-Cyano-4'-methyl-5-(2,2,2-trifluoro-1-hydroxyethyl)biphenyl-3-carboxylic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a stirred solution of methyl 2′-cyano-4′-methyl-5-(2,2,2-trifluoro-1-hydroxyethyl)biphenyl-3-carboxylate (250 mg, 0.72 mmol) in 1,4-dioxane (5 mL) and water (2.5 mL) was added lithium hydroxide (50 mg, 2.1 mmol). The reaction mixture was stirred at rt for 4 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 (CDCl3, 400 MHz): 8.27 (s, 1H), 8.24 (s, 1H), 7.95 (s, 1H), 7.58 (s, 1H), 7.48 and 7.43 (AB, J=8.0 Hz, 2H), 5.17 (q, J=6.4 Hz, 1H), 2.43 (s, 3H).

後処理

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

出典と根拠

ORDレコード
ord-13bb4607081a42febc678ab476c0ab33
出典データセット
uspto-grants-2015_02
特許番号
US08946439B2

反応ノート

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