Carbon Dioxide → 3-Dodecyl-5-isoxazole acetic acid
Reaktionsgleichung
[CH2:1]([C:13]1[CH:17]=[C:16]([CH3:18])[O:15][N:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C([Li])CCC.[C:24](=[O:26])=[O:25]>O1CCCC1>[CH2:1]([C:13]1[CH:17]=[C:16]([CH2:18][C:24]([OH:26])=[O:25])[O:15][N:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -75 °C
Versuchsvorschrift
To a cold (-75° C.), stirred suspension of 3-dodecyl-5-methylisoxazole (3.40 g, 0.0135 mol) in dry tetrahydrofuran (900 mL) was added in one portion a 1.6M solution (8.5 mL, 0.014 mol) of n-butyl lithium in hexanes, and the mixture was stirred for 1.5 hours. The mixture was poured onto freshly crushed dry ice and allowed to warm overnight. The mixture was rotoevaporated, and the residue was partitioned between petroleum ether and 0.5M NaOH. The aqueous layer was washed (petroleum ether), acidified with concentrated hydrochloric acid to pH ~1-2, and extracted (CHCl3). The extract was dried (MgSO4) and rotoevaporated to a waxy solid. The solid was recrystallized from toluene to give a white solid; yield 0.65 g (16%); mp 79°-80° C.
Aufarbeitung
- stirringthe mixture was stirred for 1.5 hours
- temperatureto warm overnight
- customthe residue was partitioned between petroleum ether and 0.5M NaOH
- washThe aqueous layer was washed (petroleum ether)
- extractionextracted (CHCl3)
- dry with materialThe extract was dried (MgSO4)
- customThe solid was recrystallized from toluene
- customto give a white solid
Quellen und Nachweise
- ORD-Eintrag
- ord-26031ff77c434ae4bd5edc82cb8a0dd8
- Quelldatensatz
- uspto-grants-1994_11
- Patentnummer
- US05366987
Notizen zur Reaktion
Wird geladen…