N,N-diethyl-4-formylbenzamide → 4-(N,N-diethylcarbamoyl)benzhydryl alcohol
Reaktionsgleichung
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:9]([C:11]1[CH:23]=[CH:22][C:14]([C:15]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=1)=[O:10]>O1CCCC1>[CH2:20]([N:17]([CH2:18][CH3:19])[C:15]([C:14]1[CH:22]=[CH:23][C:11]([CH:9]([OH:10])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:12][CH:13]=1)=[O:16])[CH3:21]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
Phenylmagnesium bromide (1.0 M solution in tetrahydrofuran, 235 mL, 235 mmol) was slowly added to a flask containing a cold (−78° C.) solution of 4-formyl-N,N-diethylbenzamide (48.18 g, 235 mmol) in 500 mL of dry tetrahydrofuran under nitrogen. The transfer rate was monitored to maintain reaction temperature below −70° C. The reaction was stirred for another 45 minutes at −78° C. and then quenched with 45 mL of saturated aqueous ammonium chloride. After warming to room temperature, the mixture was diluted with 900 mL of diethyl ether and washed with 900 mL of water followed by 230 mL of saturated sodium chloride. The ethereal solution was dried over sodium sulfate and the solvent removed to give crude 4-(N,N-diethylcarbamoyl)benzhydryl alcohol as a light yellow oil. Crude yield was ˜92%.
Aufarbeitung
- temperatureto maintain
- customreaction temperature below −70° C
- customquenched with 45 mL of saturated aqueous ammonium chloride
- temperatureAfter warming to room temperature
- additionthe mixture was diluted with 900 mL of diethyl ether
- washwashed with 900 mL of water
- dry with materialThe ethereal solution was dried over sodium sulfate
- customthe solvent removed
Quellen und Nachweise
- ORD-Eintrag
- ord-c5026d84660d4697846fe207679b8ea8
- Quelldatensatz
- uspto-grants-2014_10
- Patentnummer
- US08865721B2
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