Sodium hydride → (R)-4-[2-nitro-5-(thiophen-3-ylmethoxy)phenoxy]-4-(2-methylphenyl)butyric acid

HRID 322918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 322918
[OH:1][C@@H:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14])[CH2:3][CH2:4][C:5]([O-:7])=[O:6].[Na+].[H-].[Na+].F[C:19]1[CH:24]=[C:23]([O:25][CH2:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)[CH:22]=[CH:21][C:20]=1[N+:32]([O-:34])=[O:33]>C1COCC1>[N+:32]([C:20]1[CH:21]=[CH:22][C:23]([O:25][CH2:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)=[CH:24][C:19]=1[O:1][C@@H:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14])[CH2:3][CH2:4][C:5]([OH:7])=[O:6])([O-:34])=[O:33]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 220101462-Fluoro-4-(3-thienylmethoxy)nitrobenzeneHCID 86756593Sodium (R)-4-Hydroxy-4-(2-methylphenyl)butanoate

Produkt 1

HCID 53638071(R)-4-[2-nitro-5-(thiophen-3-ylmethoxy)phenoxy]-4-(2-methylphenyl)butyric acidAusbeute 18,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A stirred suspension of sodium (R)-4-hydroxy-4-(2-methylphenyl)butanoate (190 mg) in THF (15 mL) is treated with 60% sodium hydride (35 mg) and maintained at 25° for 0.5 hours. The mixture is treated with 2-fluoro-4-(thiophen-3-ylmethoxy)nitrobenzene (220 mg) and maintained at 50° C. for 3 hours. The solution is evaporated. The residue is dissolved in ethyl acetate, washed with water, dried and evaporated. The residue is purified by flash chromatography on silica, eluting with dichloromethane followed by ethyl acetate, followed by recrystallisation from ethyl acetate/pentane to give (R)-4-[2-nitro-5-(thiophen-3-ylmethoxy)phenoxy]-4-(2-methylphenyl)butyric acid (70 mg), a tan coloured solid, mp. 130-131° C. 1H NMR (CHCl3) 2.2-2.9 (4H,m), 2.4 (3H,s), 4.9 (2H, q), 5.5 (1H, q), 6.2 (1H,s), 6.5 (1H,d), 7.0-7.4 (7H,m), 7.9 (1H,d).

Aufarbeitung

  1. temperaturemaintained at 25° for 0.5 hours
  2. customThe solution is evaporated
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customThe residue is purified by flash chromatography on silica
  8. washeluting with dichloromethane
  9. customfollowed by recrystallisation from ethyl acetate/pentane

Quellen und Nachweise

ORD-Eintrag
ord-cad6a049ca96463ca497196a04994815
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211234B1

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