Toluene → HCID 140408675, compound

HRID 1108149Notes

Reaction equation

HRID 1108149 reaction equation
[C:1]1([C:7]2([CH2:16][C:17](CC3(C4C=CC=CC=4)CC3C3C=CC=CC=3)=O)[CH2:9][CH:8]2[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:35][O:36]/[N:37]=[C:38](\[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[CH2:48][O:49][NH2:50])/[C:39]([O-:41])=[O:40].[C:51]1(C)C=CC=CC=1>>[C:1]1([C:7]2([C:16](=[N:50][O:49][CH2:48][C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=3/[C:38](=[N:37]\[O:36][CH3:35])/[C:39]([O:41][CH3:51])=[O:40])[CH3:17])[CH2:9][CH:8]2[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 54448459HCID 54448459, compoundHCID 178502839HCID 178502839, compound

Product 1

HCID 140408675HCID 140408675, compound

Procedure

To a 50 ml round bottom flask equipped with magnetic stirrer and reflux condenser was charged the 0.8 g (0.0034 moles, 1.0 eq.) of 1,2-diphenylcyclopropylmethyl ketone 50 mls of anhydrous toluene, approximately 20 4A molecular sieves, and 0.9 g (0.0037 moles, 1.1 eq.) of (E)-2-(aminooxymethyl)phenylglyoxylate O-methyloxime. The reaction was refluxed for a total of 2.5 hours, then cooled, and filtered through filter paper to remove the insoluble material. The filtrate was poured into 100 mls of water and extracted with 3×50 mls of ether. The ether extract was then washed with 2×100 mls of water, 100 mls of saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated on a rotary evaporator to afford 1.4 g of a thick amber liquid which was chromatographed on silica gel with 20% ethyl acetate, 80% hexane. The pure fractions were combined and concentrated on a rotary evaporator to afford 460 mg of a thick clear colorless oil (30% isolated yield) consistent with the desired product, (E)-Methyl 2-[2-((((1-(1,2-diphenylcyclopropyl)ethylidene)amino)-oxy)methyl)phenyl]-2-methoxyiminoacetate upon analysis by 300 MHz 1H NMR.

Workup

  1. customTo a 50 ml round bottom flask equipped with magnetic stirrer
  2. temperaturereflux condenser
  3. temperatureThe reaction was refluxed for a total of 2.5 hours
  4. temperaturecooled
  5. filtrationfiltered
  6. filtrationthrough filter paper
  7. customto remove the insoluble material
  8. additionThe filtrate was poured into 100 mls of water
  9. extractionextracted with 3×50 mls of ether
  10. extractionThe ether extract
  11. washwas then washed with 2×100 mls of water, 100 mls of saturated aqueous sodium chloride solution
  12. dry with materialdried over anhydrous magnesium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-2596fbf11b74417da8c643629eca31ca
Source dataset
uspto-grants-2000_05
Patent number
US06063956

Reaction notes

Loading…