Lithium hydroxide, monohydrate → (R)-1-[5-(3-chloro-phenyl)-isoxazol-3-yl]-ethanol

HRID 1453802Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1453802
C([O:4][C@@H:5]([C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[O:9][N:8]=1)[CH3:6])(=O)C.O.[OH-].[Li+]>C1COCC1.O>[Cl:18][C:14]1[CH:13]=[C:12]([C:10]2[O:9][N:8]=[C:7]([C@H:5]([OH:4])[CH3:6])[CH:11]=2)[CH:17]=[CH:16][CH:15]=1

Komponenten

4

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 44605723(1R)-1-[5-(3-chlorophenyl)isoxazol-3-yl]ethyl acetate

Produkt 1

HCID 46701926(R)-1-[5-(3-chloro-phenyl)-isoxazol-3-yl]-ethanolAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

(1R)-1-[5-(3-chlorophenyl)isoxazol-3-yl]ethyl acetate (56 g, 211 mmol) and lithium hydroxide monohydrate (10.6 g, 253 mmol) were mixed with THF/Water (7/5, 1.2 L) and stirred at r.t. over night. Reducing the volume of the mixture in vacuo to about ½, followed by dilution with brine, extraction with ether and then drying over MgSO4 and in vacuo concentration gave crude product. The crude product was purified by flash column chromatography on silica using heptane/EtOAc=70:30, to give the title compound (40 g, 85%). 1H NMR: 7.73 (m, 1H), 7.63 (m, 1H), 7.38 (m, 2H), 6.57 (s, 1H), 5.07 (q, 1H), 2.44 (s, 1H), 1.59 (d, 3H).

Aufarbeitung

  1. extractionfollowed by dilution with brine, extraction with ether
  2. dry with materialdrying over MgSO4 and in vacuo concentration
  3. customgave crude product
  4. customThe crude product was purified by flash column chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-b97e1fb0d44e4c33a47251d88b95c6bf
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07476684B2

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