m-Chloroperbenzoic acid → HCID 89963242, compound

HRID 337798Notes

Reaction equation

HRID 337798 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][N:10]=[N:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:21])C=1>ClCCl.[Ni].C(O)C>[N:10]1[CH:11]=[CH:12][C:7]([C@H:1]2[CH2:6][CH2:5][CH2:4][CH2:3][C@@H:2]2[OH:21])=[CH:8][N:9]=1

Participants

6

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 899628934-Cyclohex-1-en-1-ylpyridazine

Product 1

HCID 89963242HCID 89963242, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the 4-(cyclohex-1-en-1-yl)pyridazine (0.15 g, 0.94 mmol) prepared in Example 53a in dichloromethane (9.4 mL), 3-chloroperbenzoic acid (0.76 g, 3.09 mmol) was added with cooling on ice, and the reaction solution was stirred at room temperature for 4 hours. A highly polar compound was removed with a silica gel pad (dichloromethane) to yield crude epoxide. A solution of the crude epoxide and Raney nickel in ethanol (3.0 mL) was stirred at 70° C. for 3 hours under a hydrogen atmosphere. The reaction solution was filtered, and the residue was then purified with silica gel chromatography to yield the title compound (35 mg, 31%) as a colorless amorphous solid.

Workup

  1. temperaturewith cooling on ice
  2. customA highly polar compound was removed with a silica gel pad (dichloromethane)
  3. customto yield crude epoxide
  4. filtrationThe reaction solution was filtered
  5. customthe residue was then purified with silica gel chromatography

Sources & evidence

ORD record
ord-33b8ad3a5e3046a1b1d27b34d45a0352
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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