Sodium hydride → (RS)-4-(benzo[1,3]dioxol-4-yl)-4-[2-cyano-5-(3-pyridylmethoxy)phenoxy]butanoic acid

HRID 322904

反応式

HRID 322904 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH:10]([OH:16])[CH2:11][CH2:12][C:13]([O-:15])=[O:14])[C:4]=2[O:3][CH2:2]1.[Na+].[H-].[Na+].F[C:21]1[CH:28]=[C:27]([O:29][CH2:30][C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)[CH:26]=[CH:25][C:22]=1[C:23]#[N:24]>O1CCCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH:10]([O:16][C:25]3[CH:26]=[C:27]([O:29][CH2:30][C:31]4[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=4)[CH:28]=[CH:21][C:22]=3[C:23]#[N:24])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])[C:4]=2[O:3][CH2:2]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 220104982-Fluoro-4-(3-pyridylmethoxy)benzonitrileHCID 86756589sodium (RS)-4-(benzo[1,3]dioxol-4-yl)-4-hydroxybutanoate

生成物 1

HCID 22010433(RS)-4-(benzo[1,3]dioxol-4-yl)-4-[2-cyano-5-(3-pyridylmethoxy)phenoxy]butanoic acid収率 39.5%

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-(benzo[1,3]dioxol-4-yl)-4-hydroxybutanoate (1.23 g) is added to a stirred suspension of sodium hydride (0.6 g, 60% dispersion in mineral oil) in tetrahydrofuran (50 mL). The mixture is stirred at room temperature for 1.5 hours when 2-fluoro-4-(3-pyridylmethoxy)benzonitrile (1.07 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 2 with 1 N hydrochloric acid and the mixture extracted with ethyl acetate (100 mL). The organic phase is washed with water (100 mL), with brine (100 mL), dried over magnesium sulphate and evaporated. The yellow semi-solid residue is recrystallised from acetonitrile to give (RS)-4-(benzo[1,3]dioxol-4-yl)-4-[2-cyano-5-(3-pyridylmethoxy)phenoxy]butanoic acid (0.80 g) as a cream solid, m.p. 181-183° C. [Elemental analysis:- C,66.32; H,4.57; N,6.52%. Calculated :- C,66.66; H,4.66; N,6.48%]

後処理

  1. additionis added in one portion
  2. customevaporated
  3. dissolutionThe residue is dissolved in water (100 mL)
  4. extractionthe mixture extracted with ethyl acetate (100 mL)
  5. washThe organic phase is washed with water (100 mL), with brine (100 mL)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customThe yellow semi-solid residue is recrystallised from acetonitrile

出典と根拠

ORDレコード
ord-679a2a5cfb1b4d3c91ea42c2fed92847
出典データセット
uspto-grants-2001_04
特許番号
US06211234B1

関連ノート

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