Butyl vinyl ether → HCID 67168980, compound

HRID 1517583Notes

Reaction equation

HRID 1517583 reaction equation
[C:1]1(C2C3C(=C4C(=CC=3)C(C3C=CC=CC=3)=CC=N4)N=CC=2)C=CC=C[CH:2]=1.C(OCCCC)=C.[CH2:34]([O:36][C:37]([C:39]1[C:40]([CH3:52])=[N:41][N:42]([C:44]2[C:49]([CH2:50][OH:51])=[CH:48][CH:47]=[CH:46][N:45]=2)[CH:43]=1)=[O:38])[CH3:35]>C(N(CC)CC)C.FC(F)(F)C([O-])=O.[Pd+2].FC(F)(F)C([O-])=O>[CH3:52][C:40]1[C:39]([C:37]([O:36][CH2:34][CH3:35])=[O:38])=[CH:43][N:42]([C:44]2[C:49]([CH2:50][O:51][CH:1]=[CH2:2])=[CH:48][CH:47]=[CH:46][N:45]=2)[N:41]=1

Participants

6

Reactant 3

HCID 8108Butyl vinyl etherHCID 728124,7-Diphenyl-1,10-phenanthrolineHCID 67168013HCID 67168013, compound

Product 1

HCID 67168980HCID 67168980, compoundYield 67.9%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 2733347Palladium(II) trifluoroacetateCatalyst

Conditions

Temperature
75 °C

Procedure

Palladium(II)trifluoroacetate (5.1 mg, 15.3 mmoles) and 4,7-diphenyl-phenanthroline (5.1 mg, 15.3 mmoles) are dissolved in n-butyl vinyl ether (6.1 mL, 61.2 mmol) and 1-(3-hydroxymethyl-pyridin-2-yl)-3-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (800 mg, 3.1 mmol) and a few drops of triethylamine are added. The flask is sealed and stirred at 75° C. for 24 hours. Then the mixture is cooled to 24° C. and filtrated through a pad of celite. The solvent is eliminated under reduced pressure and the residue is purified by normal phase Isco chromatography using hexane and ethyl acetate as eluents (5-20% in ethyl acetate) to give 605 mg of ethyl 3-methyl-1-[3-(vinyloxymethyl)-2-pyridyl]pyrazole-4-carboxylate. MS (m/z): 288 (M+1)

Workup

  1. customThe flask is sealed
  2. temperatureThen the mixture is cooled to 24° C.
  3. filtrationfiltrated through a pad of celite
  4. customthe residue is purified by normal phase Isco chromatography

Sources & evidence

ORD record
ord-3063828a5a154972aee2037b0c3794c8
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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