m-Chloroperbenzoic acid → HCID 66714742, compound

HRID 1470554Notes

Reaction equation

HRID 1470554 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[F:12][C:13]([F:34])([F:33])[C:14]1[CH:15]=[C:16]([C:20]2[N:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:22][CH:21]=2)[CH:17]=[CH:18][CH:19]=1>C(Cl)Cl>[CH2:31]([O:30][C:28](=[O:29])/[CH:27]=[CH:26]/[C:23]1[CH:22]=[CH:21][C:20]([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:13]([F:33])([F:12])[F:34])[CH:15]=2)=[N+:25]([O-:9])[CH:24]=1)[CH3:32]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86691196HCID 86691196, compound

Product 1

HCID 66714742HCID 66714742, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-CPBA (13.9 g, 80.97 mmol) was added portion wise to a solution of trans-ethyl 3-(6-(3-(trifluoromethyl)phenyl)pyridin-3-yl)acrylate (13 g, 40.47 mmol) in DCM (150 mL) at 0° C. over a period of 30 min. and stirred at RT for 16 h. After completion, the reaction mixture was poured into ice water (100 mL), extracted with DCM (2×100 mL). Combined organic extracts were treated with sodium metabisulphite, washed with water (100 mL), brine (100 mL), dried over anhydrous Na2SO4, filtered and evaporated. The crude residue was purified by column chromatography (SiO2) by using MeOH:chloroform (1:99) to afford (9 g, 66%) (E)-5-(3-ethoxy-3-oxoprop-1-enyl)-2-(3-(trifluoromethyl)phenyl)pyridine 1-oxide as yellow solid.

Workup

  1. extractionextracted with DCM (2×100 mL)
  2. additionCombined organic extracts were treated with sodium metabisulphite
  3. washwashed with water (100 mL), brine (100 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude residue was purified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-ca46bdb1d8fd4231a65df41839f665fa
Source dataset
uspto-grants-2015_04
Patent number
US09006449B2

Reaction notes

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