Diisobutylaluminum hydride → 5-(4-Trifluoromethylphenyl)pentanal

Temperature

-60 °C

The above 5-(4-trifluoromethylphenyl)pentanoic acid ethylester 12.2 g (44.5 mmol) was stirred in toluene 70 ml while the temperature was cooled to −60° C., and a 1.01 M of toluene solution 46.0 ml (46.5 mmol) of DIBAL was added dropwise, and the mixture was stirred at −60° C. for 15 minutes. At the same temperature, a saturated ammonium chloride aqueous solution 40 ml was added dropwise to the reactant, and the mixture was heated to room temperature and stirred for 30 minutes. Diethyl ether 100 ml was added to the reactant, and the mixture was stirred at room temperature for one hour, and magnesium sulfate was added, and the suspension was filtered with cerite. The filtrate was washed with water, the organic layer was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: toluene) to obtain 5-(4-trifluoromethylphenyl)pentanal 7.50 g (32.6 mmol). The yield was 73.3% from 5-(4-trifluorophenyl)pentanoic add ethylester.

1. temperaturethe mixture was heated to room temperature
2. stirringstirred for 30 minutes
3. stirringthe mixture was stirred at room temperature for one hour
4. filtrationthe suspension was filtered with cerite
5. washThe filtrate was washed with water
6. dry with materialthe organic layer was dried over magnesium sulfate
7. distillationthe solvent was distilled off under reduced pressure
8. customThe residue was purified by silica gel column chromatography (eluent: toluene)

ORD record

ord-74ef1ab5335545389afa38a35b372046

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06235355B1