Sodium hydride → (RS)-4-[2-cyano-5-(3-pyridylmethoxy)-phenoxy]-4-(2,3-dimethylphenyl)butanoic acid

HRID 322905ノート

反応式

HRID 322905 の反応式
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([OH:15])[CH2:10][CH2:11][C:12]([O-:14])=[O:13].[Na+].[H-].[Na+].F[C:20]1[CH:27]=[C:26]([O:28][CH2:29][C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[CH:25]=[CH:24][C:21]=1[C:22]#[N:23]>O1CCCC1>[C:22]([C:21]1[CH:24]=[CH:25][C:26]([O:28][CH2:29][C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)=[CH:27][C:20]=1[O:15][CH:9]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=1[CH3:1])[CH2:10][CH2:11][C:12]([OH:14])=[O:13])#[N:23]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 220104982-Fluoro-4-(3-pyridylmethoxy)benzonitrileHCID 86756590sodium (RS)-4-(2,3-dimethylphenyl)-4-hydroxybutanoate

生成物 1

HCID 22010143(RS)-4-[2-cyano-5-(3-pyridylmethoxy)-phenoxy]-4-(2,3-dimethylphenyl)butanoic acid収率 47%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
57.5 °C

実験手順

A solution of sodium (RS)-4-(2,3-dimethylphenyl)-4-hydroxybutanoate (1 g) is added to a stirred suspension of sodium hydride (0.5 g, 60% dispersion in mineral oil) in tetrahydrofuran (50 mL) under nitrogen. The mixture is stirred at room temperature for 3 hours when 2-fluoro-4-(3-pyridylmethoxy)benzonitrile (1 g) is added in one portion. The reaction mixture is heated at 55-60° C. for 18 hours and evaporated. The residue is dissolved in water (100 mL), the solution acidified to pH 1 with 1 N hydrochloric acid. The precipitated solid Is filtered, washed with water, ethyl acetate and ether, dried, and recrystallised from ethyl acetate to give (RS)-4-[2-cyano-5-(3-pyridylmethoxy)-phenoxy]-4-(2,3-dimethylphenyl)butanoic acid (0.85 g) as a white solid, m.p. 187-189° C. [Elemental analysis:- C,71.76; H,6.59; N,5.67%. Calculated:- C,72.10; H,6.73; N,5.81%]

後処理

  1. additionis added in one portion
  2. customevaporated
  3. dissolutionThe residue is dissolved in water (100 mL)
  4. filtrationThe precipitated solid Is filtered
  5. washwashed with water, ethyl acetate and ether
  6. customdried
  7. customrecrystallised from ethyl acetate

出典と根拠

ORDレコード
ord-9ffcb8afca044114a77ae7bca558916f
出典データセット
uspto-grants-2001_04
特許番号
US06211234B1

反応ノート

読み込み中…