HCID 86713806, compound → HCID 86713808, compound

HRID 521859Notes

Reaction equation

HRID 521859 reaction equation
[CH2:1]([O:4][CH2:5][CH:6]([C:10]1[N:14]([CH3:15])[N:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17])[CH2:7][CH:8]=[CH2:9])C=C>Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl.C1(C)C=CC=CC=1>[CH3:15][N:14]1[C:10]([CH:6]2[CH2:7][CH2:8][CH:9]=[CH:1][O:4][CH2:5]2)=[C:11]([N+:16]([O-:18])=[O:17])[CH:12]=[N:13]1

Participants

4

Reactant 1

HCID 86713806HCID 86713806, compound

Product 1

HCID 86713808HCID 86713808, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 178479819HCID 178479819, compoundCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
120 °C

Procedure

A solution of 1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium, “Grubb's catalyst 2nd generation”, CAS Reg. No. 246047-72-3, Sigma-Aldrich Product No. 569747, U.S. Pat. No. 6,111,121, U.S. Pat. No. 7,329,758 (375 mg, 0.42 mmol) in toluene (15 ml) was added to a solution of 5-[1-(allyloxymethyl)but-3-enyl]-1-methyl-4-nitro-pyrazole (527 mg, 2.10 mmol) in toluene (115 mL). The resulting solution was heated at reflux (120° C.) for 2.5 h. After cooling to room temperature, the solvent was removed under reduced pressure and the residue was purified via silica gel chromatography (0-100% EtOAc/heptane) to afford 1-methyl-4-nitro-5-(2,3,4,5-tetrahydrooxepin-3-yl)pyrazole (133 mg, 30%).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureAfter cooling to room temperature
  3. customthe solvent was removed under reduced pressure
  4. customthe residue was purified via silica gel chromatography (0-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-2ee64f893bbb4815be594306431700d5
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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