m-Chloroperbenzoic acid → 4-Chloromethyl-2-[2-(4-trifluoromethylsulfinyl-phenyl)-vinyl]-oxazole

HRID 750942Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 750942
[Cl:1][CH2:2][C:3]1[N:4]=[C:5]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([S:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)[O:6][CH:7]=1.ClC1C=C(C(OO)=[O:29])C=CC=1>ClCCl>[Cl:1][CH2:2][C:3]1[N:4]=[C:5]([CH:8]=[CH:9][C:10]2[CH:11]=[CH:12][C:13]([S:16]([C:17]([F:20])([F:19])[F:18])=[O:29])=[CH:14][CH:15]=2)[O:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 691129774-Chloromethyl-2-[2-(4-trifluoromethylsulfanyl-phenyl)-vinyl]-oxazole

Produkt 1

HCID 692923894-Chloromethyl-2-[2-(4-trifluoromethylsulfinyl-phenyl)-vinyl]-oxazoleAusbeute 31,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 17.6 g (55 mmol) 4-chloromethyl-2-[2-(4-trifluoromethylsulfanyl-phenyl)-vinyl]-oxazole and 14.93 g (60 mmol) 3-chloro-benzenecarboperoxoic acid in 200 ml dichloromethane was stirred at room temperature over night. After filtration, the filtrate was washed three times with sodium hydroxide solution, then with water, dried over sodium sulfate, filtered and evaporated. Purification on silica, after elution with heptane/ethyl acetate 5:1, yielded 5.78 g (31%) 4-chloromethyl-2-[2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazole as off-white solid melting at 102-104° C.

Aufarbeitung

  1. filtrationAfter filtration
  2. washthe filtrate was washed three times with sodium hydroxide solution
  3. dry with materialwith water, dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customPurification on silica
  7. washafter elution with heptane/ethyl acetate 5:1

Quellen und Nachweise

ORD-Eintrag
ord-e2fa77b8158640efa969d8dee9c2e908
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405231B2

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