Ammonium Chloride → 3-[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]-1-propanol

HRID 2423443Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2423443
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH2:14][CH2:15][CH:16]=[O:17])=[C:12]([CH:18]([CH3:20])[CH3:19])[O:11][N:10]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[C:13]([CH2:14][CH2:15][CH2:16][OH:17])=[C:12]([CH:18]([CH3:20])[CH3:19])[O:11][N:10]=1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 593215603-[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]propanal

Produkt 1

HCID 593215873-[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]-1-propanolAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 3-[3-(2,6-dichlorophenyl)-5-(1-methylethyl) -4-isoxazolyl]propanal (220 mg, 0.705 mmol) in methanol (7 mL) at 0° C. was added sodium borohydride (67 mg, 1.8 mmol). The solution was stirred at 0° C. for approximately 20 minutes and was then poured into aqueous ammonium chloride. The mixture was extracted twice with ether. The combined organic layers were dried over magnesium sulfate and concentrated to afford 3-[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]-1-propanol (204 mg, 92%). 1H-NMR (400 MHz, CDCl3) δ 7.42-7.28 (m, 3H), 3.53 (t, J=6 Hz, 2H), 3.21 (septet, J=7 Hz, 1H), 3.35 (t, J=8 Hz, 2H), 1.57-1.50 (m, 2H), 1.38 (d, J=7 Hz, 6H).

Aufarbeitung

  1. extractionThe mixture was extracted twice with ether
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c7ecf939c7df43629b00fca4e4dd2e50
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960552B2

Notizen zur Reaktion

Wird geladen…