Dichloromethane → HCID 3441033, compound

HRID 1387367Notes

Reaction equation

HRID 1387367 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.CC(=NOC[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])C1C=CC=C(C(F)(F)F)C=1.ClCCl>CO>[CH3:46][O:45][N:44]=[C:39]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:33]=1)[CH:40]=[O:41]

Participants

5

Reactant 3

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

Product 1

HCID 3441033HCID 3441033, compoundYield 109.6%

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-6510a90b7cb8415bb41757fbc291ce42
Source dataset
uspto-grants-2001_07
Patent number
US06268312B1

Reaction notes

Loading…