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

HRID 322905

Reaktionsgleichung

[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]

Komponenten

Reaktionsbedingungen

Temperatur: 57.5 °C

Versuchsvorschrift

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%]

Aufarbeitung

additionis added in one portion
customevaporated
dissolutionThe residue is dissolved in water (100 mL)
filtrationThe precipitated solid Is filtered
washwashed with water, ethyl acetate and ether
customdried
customrecrystallised from ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-9ffcb8afca044114a77ae7bca558916f
Quelldatensatz: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06211234B1

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