Dichloromethane → 2-(2,5-Dimethylphenoxymethyl)-alpha-methoxyiminophenylacetaldehyde
Reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[CH3:18][C:19]1[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][C:20]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29](=[N:34][O:35][CH3:36])[C:30](OC)=[O:31].ClCCl>CO>[CH3:18][C:19]1[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][C:20]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29](=[N:34][O:35][CH3:36])[CH:30]=[O:31]Participants
5
Procedure
1M diisobutylaluminum hydride/toluene solution (5.5 ml, 5.5 mmol) was added dropwise to a mixture of methyl 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetate (1.64 g, 5 mmol) and dichloromethane (15 ml) at −70° C. over 0.5 hours, and then the mixture was stirred at −70° C. to room temperature for 3 hours. Methanol (3 ml) was added to the reaction mixture, and the mixture was stirred at room temperature for 1 hour. The precipitated insoluble materials were removed, and the mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetaldehyde (0.54 g, 36.3%) as a colorless oil.
Workup
- stirringthe mixture was stirred at room temperature for 1 hour
- customThe precipitated insoluble materials were removed
- concentrationthe mixture was concentrated under reduced pressure
- customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetaldehyde (0.54 g, 36.3%) as a colorless oil
Sources & evidence
- ORD record
- ord-4216626b26c94b0ca69a53f78dd71bb7
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06362212B1
Reaction notes
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