m-Chloroperbenzoic acid → HCID 19038008, compound

HRID 1604021Notes

Reaction equation

HRID 1604021 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[N:16][C:17]([CH3:20])=[CH:18][CH:19]=2)=[CH:5][CH:4]=1.[CH:21]1C=C(Cl)C=[C:23]([C:28]([O:30]O)=[O:29])[CH:22]=1>C(Cl)Cl>[C:28]([CH2:23]/[CH:22]=[CH:21]/[C:15]1[C:14]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[CH:19][CH:18]=[C:17]([CH3:20])[N:16]=1)([OH:30])=[O:29]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67874804HCID 67874804, compound

Product 1

HCID 19038008HCID 19038008, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-E-2-Carboxymethylethenyl)-3-[4-(4-methoxyphenyl) butyloxy]-6-methylpryidine (13.6 g, 38.2 mmol) was dissolved in dry CH2Cl2 (100 mL) and cooled to 0° C. To this was added 50% mCPBA (13.2 g, 38.3 mmol) in three portions over 10 minutes. The cooling bath was removed and the reaction was stirred for 15 h at room temperature. The reaction was poured into aqueous NaHCO3 and the product extracted into CH2Cl2. The organic extract was washed with H2O and brine and dried (MgSO4). The crude product was obtained as a yellow solid and was used without further purification.

Workup

  1. customThe cooling bath was removed
  2. additionThe reaction was poured into aqueous NaHCO3
  3. extractionthe product extracted into CH2Cl2
  4. extractionThe organic extract
  5. washwas washed with H2O and brine
  6. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-b574a461353746cea2f9fadc9782fb3c
Source dataset
uspto-grants-1999_11
Patent number
US05990314

Reaction notes

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