Sodium borohydride → [5-(3-Chlorophenyl)isoxazol-3-yl]methanol

HRID 1453798Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1453798
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[O:14][N:13]=[C:12]([C:15](OCC)=[O:16])[CH:11]=2)[CH:7]=[CH:8][CH:9]=1>CO>[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[O:14][N:13]=[C:12]([CH2:15][OH:16])[CH:11]=2)[CH:7]=[CH:8][CH:9]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 46929188Ethyl 5-(3-chlorophenyl)isoxazole-3-carboxylate

Produkt 1

HCID 57528605[5-(3-Chlorophenyl)isoxazol-3-yl]methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Sodium borohydride (96.7 g, 2.6 mol) was slowly added to a solution of ethyl 5-(3-chlorophenyl)isoxazole-3-carboxylate (214.5 g, 0.85 mol) in methanol (2.5 L) at 0° C. The reaction mixture was heated at 50° C. for 2 h and was quenched with EtOAc at r.t. Most of the solvent was distilled off and to the remaining crude was added EtOAc. The organic layer was washed with water, saturated brine and concentrated to give the title compound, which was used directly in the next step. MS (M++1)=210.

Aufarbeitung

  1. customwas quenched with EtOAc at r.t
  2. distillationMost of the solvent was distilled off and to the remaining crude
  3. additionwas added EtOAc
  4. washThe organic layer was washed with water, saturated brine
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-12c5278033dc4b20816c3773871ca6c2
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07476684B2

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