HCID 13671387, compound → Cyano(6-phenoxy-2-pyridinyl)methyl 2,2-dimethyl-3-((isobutoxyimino)methyl)cyclopropanecarboxylate

HRID 1380908Notes

Reaction equation

HRID 1380908 reaction equation
[CH3:1][C:2]1([CH3:15])[CH:4]([CH:5]=[N:6][O:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH:3]1[C:12]([OH:14])=[O:13].S(C1C=CC(C)=CC=1)(O[CH:20]([C:34]#[N:35])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:22]=1)(=O)=O>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])[O-].[K+].[K+].O>[CH3:15][C:2]1([CH3:1])[CH:4]([CH:5]=[N:6][O:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH:3]1[C:12]([O:14][CH:20]([C:34]#[N:35])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:22]=1)=[O:13]

Participants

7

Reactant 2

HCID 13671387HCID 13671387, compoundHCID 537760262,2-Dimethyl-3-((isobutoxyimino)methyl)cyclopropanecarboxylic acid

Product 1

HCID 53795267Cyano(6-phenoxy-2-pyridinyl)methyl 2,2-dimethyl-3-((isobutoxyimino)methyl)cyclopropanecarboxylateYield 9.6%

Reagents, catalysts & solvents 4

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 0.95 g of 2,2-dimethyl-3-((isobutoxyimino)methyl)cyclopropanecarboxylic acid and 1.70 g of cyano(6-phenoxy-2-pyridinyl)methyl tosylate in 30 ml of toluene was added 200 mg of tetrabutylammonium hydrogen sulfate. To this mixture was added in one portion 0.75 g of potassium carbonate dissolved in 10 ml of water. The reaction mixture turned from yellow to bright purple in 30 seconds. The reaction mixture was stirred vigorously and heated to 75° C. The purple color disappeared after 10 minutes. The reaction mixture was heated for four hours at 70° C. and then cooled to room temperature. The resulting mixture was washed with 100 ml of 5% potassium carbonate solution and extracted thrice with 50 ml portions of diethyl ether. The combined extract was stripped to give 440 mg of a crude oil. This crude product was chromatographed using 30% diethyl ether in hexane as eluent. The product was washed off the silica with ethyl acetate and the eluate was stripped to give 180 mg of the desired product as a yellow oil.

Workup

  1. custombright purple in 30 seconds
  2. temperatureThe reaction mixture was heated for four hours at 70° C.
  3. temperaturecooled to room temperature
  4. washThe resulting mixture was washed with 100 ml of 5% potassium carbonate solution
  5. extractionextracted thrice with 50 ml portions of diethyl ether
  6. extractionThe combined extract
  7. customto give 440 mg of a crude oil
  8. customThis crude product was chromatographed
  9. washThe product was washed off the silica with ethyl acetate

Sources & evidence

ORD record
ord-9738e58f74df47eba7096f33966f7610
Source dataset
uspto-grants-1986_04
Patent number
US04584304

Reaction notes

Loading…