Water → HCID 14687817, Verbindung
Reaktionsgleichung
C[O:2][C:3](=O)[CH2:4][CH:5]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:17].[BH4-].[Na+].O>C(O)(C)C>[OH:2][CH2:3][CH2:4][CH:5]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[OH:17]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
The crude ketoester (IX) from step 4 (approximately 180 gm; 0.7 mol) was refluxed for 8 hours with agitation under nitrogen with 74 gm (1.96 mol) of sodium borohydride in 1250 ml of isopropanol. After addition of 150 ml of water, the mixture was agitated for 30 minutes at 60° C., and any sodium borohydride remaining was destroyed by the addition of 100 ml of acetone with good cooling. After agitation for another 30 minutes, the isopropanol was distilled off with the simultaneous addition of 200 ml water. After cooling to approximately 30° to 35° C., the residue was neutralized with half-concentrated sulfuric acid and mixed with 700 ml of toluene. The aqueous phase was separated. The toluene phase contained approximately 135 gm of 1,4-diol (IV) (85% yield) and was used further without evaporation.
Aufarbeitung
- customany sodium borohydride remaining was destroyed by the addition of 100 ml of acetone with good cooling
- waitAfter agitation for another 30 minutes
- distillationthe isopropanol was distilled off with the simultaneous addition of 200 ml water
- temperatureAfter cooling to approximately 30° to 35° C.
- additionmixed with 700 ml of toluene
- customThe aqueous phase was separated
Quellen und Nachweise
- ORD-Eintrag
- ord-c5f2e0713231436ca1cf13bf8a2eab0f
- Quelldatensatz
- uspto-grants-1982_11
- Patentnummer
- US04360468
Notizen zur Reaktion
Wird geladen…