Sodium Chloride → 3-Ethoxybenzo[D]isoxazol-6-OL

HRID 468548

Reaktionsgleichung

Reaktionsgleichung von HRID 468548
B(Br)(Br)Br.O1C2C=CC=CC=2C=N1.[CH2:14]([O:16][C:17]1[C:21]2[CH:22]=[CH:23][C:24]([O:26]C)=[CH:25][C:20]=2[O:19][N:18]=1)[CH3:15].C([O-])(O)=O.[Na+].[Na+].[Cl-]>ClCCl.O.CCCCCC.C(OCC)(=O)C>[CH2:14]([O:16][C:17]1[C:21]2[CH:22]=[CH:23][C:24]([OH:26])=[CH:25][C:20]=2[O:19][N:18]=1)[CH3:15]

Komponenten

9

Edukt 5

HCID 5234Sodium ChlorideHCID 25134Boron tribromideHCID 710731,2-BenzisoxazoleHCID 516892Sodium BicarbonateHCID 210778053-Ethoxy-6-methoxybenzo[D]isoxazole

Produkt 1

HCID 1358487453-Ethoxybenzo[D]isoxazol-6-OL

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

Boron tribromide (1.0M solution in dichloromethane; 1.39 ml, 1.39 mmol) was added to a stirred, −78° cooled solution of benzisoxazole from part (c) (179 mg, 928 μmol) in dichloromethane (4 ml) under an argon atmosphere. The reaction mixture was gradually warmed to room temperature over approx. 2 hours, and stirred overnight. Tlc (silica, 2:1 hexane/ethyl acetate) showed new polar material as well as unreacted starting material. The reaction was worked up by adding water (5 ml) and ice. The aqueous phase was neutralized by addition of saturated NaHCO3 solution, and saturated with NaCl. The aqueous phase was extracted into dichloromethane (3×60 ml), then the organic extracts combined and washed with brine (10 ml) and dried (NaSO4). The product was purified by chromatography on silica (18 g; eluent 2.5%, 5%, then 15% ethyl acetate/hexane). The first compound to elute was unreacted 3-ethoxy-6-methoxy-1,2-benzisoxazole, (46 mg), followed by 3-ethoxy-6-hydroxy-1,2-benzisoxazole 108 mg (65%).

Aufarbeitung

  1. extractionThe aqueous phase was extracted into dichloromethane (3×60 ml)
  2. washwashed with brine (10 ml)
  3. dry with materialdried (NaSO4)
  4. customThe product was purified by chromatography on silica (18 g
  5. washThe first compound to elute

Quellen und Nachweise

ORD-Eintrag
ord-e14487a2cb074265b850a55d99405b4a
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08624025B2

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