Sodium borohydride → 2-(2-Fluoro-4-nitrophenyl)-2-methylpropane-1,3-diol

HRID 1842964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1842964
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([CH3:20])([C:16](OC)=[O:17])[C:12](OC)=[O:13].[BH4-].[Na+]>CO.O>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([CH3:20])([CH2:16][OH:17])[CH2:12][OH:13]

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 70816610Dimethyl 2-(2-fluoro-4-nitrophenyl)-2-methylmalonate

Produkt 1

HCID 708166542-(2-Fluoro-4-nitrophenyl)-2-methylpropane-1,3-diolAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of dimethyl 2-(2-fluoro-4-nitrophenyl)-2-methylmalonate (1.0 g, 3.50 mmol, 1.0 eq) in methanol (20 mL) was added NaBH4 (0.67 gm, 17.63 mmol, 5.0 eq) at 0° C. and stirred at RT for 16 h. The mixture was diluted with water (20 mL), extracted with ethyl acetate (20 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4, and the solvent was vaporated under reduced pressure. The crude product obtained was purified by CC using EtOAc/PE (2:3) to get 2-(2-fluoro-4-nitrophenyl)-2-methylpropane-1,3-diol (400 mg, 50%; TLC system: EtOAc/PE (1:1), Rf: 0.3).

Aufarbeitung

  1. extractionextracted with ethyl acetate (20 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe crude product obtained
  5. customwas purified by CC

Quellen und Nachweise

ORD-Eintrag
ord-abac8a9f448042789d7896276bdf0167
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946204B2

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