Isopropanol → 1-Quinolin-6-ylcyclopropanecarbaldehyde
Reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]1[CH2:15][O:14][CH2:13][CH2:12]1.[N:16]1[C:25]2[C:20](=[CH:21][C:22](C3(C#N)CC3)=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1.C(O)(C)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[N:16]1[C:25]2[C:20](=[CH:21][C:22]([C:11]3([CH:15]=[O:14])[CH2:13][CH2:12]3)=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -2.5 °C
Procedure
Diisobutylaluminum hydride in THF (1.0 M, 96 mL, 0.096 mol) was added to a solution of 1-quinolin-6-ylcyclopropanecarbonitrile (12.4 g, 0.0639 mol) in toluene (120 mL) at −78° C. under an atmosphere of nitrogen. The reaction mixture was allowed to warm to −5 to 0° C., and stirred at that temperature for 3 h. The mixture was re-cooled to −60° C. Isopropyl alcohol (10 mL) was carefully added dropwise. After stirring for 30 min, the mixture was warmed to −5 to 0° C. The mixture was diluted with ethyl acetate, quenched with water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over anhydrous Na2SO4, filtered through a pad of silica gel and washed with ethyl acetate in hexanes (40%). The filtrate was concentrated to yield the desired 1-quinolin-6-ylcyclopropanecarbaldehyde (12 g, 95.1%).
Workup
- temperatureThe mixture was re-cooled to −60° C
- stirringAfter stirring for 30 min
- temperaturethe mixture was warmed to −5 to 0° C
- customquenched with water
- extractionextracted with ethyl acetate
- washThe combined organic layers were washed with water and brine
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered through a pad of silica gel
- washwashed with ethyl acetate in hexanes (40%)
- concentrationThe filtrate was concentrated
Sources & evidence
- ORD record
- ord-379cabd915184830829d81aa5a265720
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08143251B2
Reaction notes
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