HCID 86617424, compound → HCID 67119205, compound

HRID 2076676Notes

Reaction equation

HRID 2076676 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N+]#N)[C:9]([O:11][CH3:12])=[O:10])=[C:4]([O:15][CH3:16])[CH:3]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[CH:8]([C:9]([O:11][CH3:12])=[O:10])[CH2:16][O:15][C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 86617424HCID 86617424, compound

Product 1

HCID 67119205HCID 67119205, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A nitrogen gas was blown into a solution of 1-(4-chloro-2-methoxyphenyl)-2-methoxy-2-oxoethanediazonium (200 mg, 0.83 mmol) obtained in Example (74-1) in toluene (5 ml) at room temperature for 5 minutes. The reaction mixture was heated to 80° C. while blowing a nitrogen gas into the mixture and tetrakis(triphenylacetate)dirhodium (II) (1 mg) was added thereto, and the mixture was stirred for 15 minutes. The reaction mixture was cooled to room temperature and the residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=5/1) to give the title compound as a pale yellow oil (127 mg, yield: 72%).

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe residue obtained
  4. customby removing the solvent under reduced pressure
  5. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-49caf2910a804859b4e301e98df96512
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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