Acetic Acid → HCID 67263626, Verbindung

HRID 1041645

Reaktionsgleichung

Reaktionsgleichung von HRID 1041645
[F:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1.C(O)(=O)C.[BH4-].[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:8]([NH:7][C:6]1[CH:11]=[C:2]([F:1])[C:3]([N+:12]([O-:14])=[O:13])=[CH:4][C:5]=1[OH:9])[CH3:10]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 136277005-Fluoro-2-methyl-6-nitro-1,3-benzoxazole

Produkt 1

HCID 67263626HCID 67263626, VerbindungAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5-Fluoro-2-methyl-6-nitro-benzoxazole (2.556 g, 13.03 mmol) was dissolved in Tetrahydrofuran (90 mL) and Acetic acid (4.5 mL, 79 mmol). Sodium borohydride (1.48 g, 39.1 mmol) was added and the reaction was stirred at room temperature for 90 min, then poured into 100 mL satd. sodium bicarbonate. The solution was extracted 3×50 mL DCM and the combined organics were washed with 1:1 brine:satd. sodium bicarbonate (50 mL) and dried over sodium sulfate, then conc. onto 10 g Celite. The crude product was chromatographed (120 g silica gel, ISCO, 0-20-40% EtOAc:Hex) to afford 2-Ethylamino-4-fluoro-5-nitro-phenol as a yellow solid (2.20 g, 84%). 1H-NMR (CDCl3): 7.55 (d, 1H, J=6.8 Hz), 6.26 (d, 1H, J=13.2 Hz), 5.51 (s, 1H), 5.05 (s, 1H), 3.26 (m, 2H), 1.34 (t, 3H, J=6.8 Hz).

Aufarbeitung

  1. additionpoured into 100 mL
  2. extractionThe solution was extracted 3×50 mL DCM
  3. washthe combined organics were washed with 1:1 brine
  4. dry with materialsodium bicarbonate (50 mL) and dried over sodium sulfate
  5. customThe crude product was chromatographed (120 g silica gel, ISCO, 0-20-40% EtOAc:Hex)

Quellen und Nachweise

ORD-Eintrag
ord-8995be8133c2489f9acb637fda7fc1be
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552186B2

Verknüpfte Notizen

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