m-Chloroperbenzoic acid → HCID 67323290, compound

HRID 1497336Notes

Reaction equation

HRID 1497336 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[N:18][CH:19]=1>C(Cl)Cl>[Cl:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[N+:18]([O-:9])[CH:19]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid3×HCID 137528915-(Chloromethyl)-2-methoxypyridine

Product 1

HCID 67323290HCID 67323290, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Chloro perbenzoic acid (mCPBA) (230 mg, 1.026 mmol) was added to a stirred, cooled 0° C. mixture of 5-(chloromethyl)-2-methoxypyridine (U1) (147 mg, 0.933 mmol) in CH2Cl2 (3731 μl). The reaction mixture was stirred at room temperature for 2 h. Another portion of mCPBA (150 mg) was added and stirred at room temperature for 4 h. A third portion mCPBA (150 mg) was added and the reaction was allowed to stir overnight. The mixture was filtered and the filtrate was concentrated. The residue was purified by silica gel flash chromatography (first 0-30% EtOAc in hexanes to remove mCPBA and SM, then 0-20% MeOH in CH2Cl2 to wash product out) to provide 5-(chloromethyl)-2-methoxypyridine 1-oxide (U2) as a white solid. ES-MS [M+1]+: 174.1.

Workup

  1. stirringstirred at room temperature for 4 h
  2. stirringto stir overnight
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel flash chromatography (first 0-30% EtOAc in hexanes
  6. customto remove mCPBA and SM
  7. wash0-20% MeOH in CH2Cl2 to wash product out)

Sources & evidence

ORD record
ord-3509b7d4643e46898046b2e3e798c0c0
Source dataset
uspto-grants-2015_12
Patent number
US09199939B2

Reaction notes

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