Dichloromethane → HCID 86755316, compound

HRID 1004391Notes

Reaction equation

HRID 1004391 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[CH3:18][C:19](=[N:30][O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:39](=[N:44][O:45][CH3:46])[C:40](OC)=[O:41])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1.ClCCl>CO>[CH3:18][C:19](=[N:30][O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:39](=[N:44][O:45][CH3:46])[CH:40]=[O:41])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 213016Methyl (methoxyimino)(2-{[({1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)acetateHCID 86583787Diisobutylaluminumhydride toluene

Product 1

HCID 86755316HCID 86755316, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1M diisobutylaluminum hydride/toluene solution (11 ml, 16.5 mmol) was added dropwise to a mixture of methyl 2-[(α-methyl-3-trifluoromethylbenzylidene)aminooxymethyl]-α-methoxyiminophenylacetate (4.83 g, 11.8 mmol) and dichloromethane (47 ml) at -65° C. or lower over 4 minutes, and the mixture was stirred at -78° C. to room temperature for 3 hours. Methanol (7 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 remaining mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 2-[(α-methyl-3-trifluoromethylbenzylidene)aminooxymethyl]-α-methoxyiminophenylacetaldehyde (2.11 g, 47.3%) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. customThe precipitated insoluble materials were removed
  3. concentrationthe remaining mixture was concentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-642534271852432aa70676cc43cfca54
Source dataset
uspto-grants-2000_04
Patent number
US06048885

Reaction notes

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