Hydrogen Peroxide → HCID 68260485, compound

HRID 884383Notes

Reaction equation

HRID 884383 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][Se]C2C=CC=CC=2[N+]([O-])=O)[N:7]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:5])[CH3:2].N1C=CC=CC=1.OO>C(Cl)Cl>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH:8]([CH:11]=[CH2:12])[N:7]1[C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 1049PyridineHCID 131729882HCID 131729882, compound

Product 1

HCID 68260485HCID 68260485, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 576 mg of selenyl ether 171 (1.22 mmol) in 15 ml of anhydrous CH2Cl2 was cooled to 0° C., added with 0.4 ml of pyridine and 0.8 ml H2O2 (30%) and stirred overnight. The intensely orange-colored solution was subsequently concentrated and purified using silica gel column chromatography (CH2Cl2) to obtain 312 mg of vinylproline 172 (1.16 mmol, 95%) as a yellowish oil.

Workup

  1. concentrationThe intensely orange-colored solution was subsequently concentrated
  2. custompurified

Sources & evidence

ORD record
ord-a565d2ae021646c48ee7431dbbccf42b
Source dataset
uspto-grants-2012_08
Patent number
US08242105B2

Reaction notes

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