3-Methylisothiazole → 5-(5-Chloropentyl)-3-methylisothiazole

HRID 2165438Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2165438
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][N:3]=1.C([Li])CCC.Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][Cl:18]>O1CCCC1.CCOCC>[Cl:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:5]1[S:4][N:3]=[C:2]([CH3:1])[CH:6]=1

Komponenten

6

Edukt 3

HCID 127473-MethylisothiazoleHCID 960701-Bromo-5-chloropentaneHCID 178418339Butyllithium

Produkt 1

HCID 200639705-(5-Chloropentyl)-3-methylisothiazoleAusbeute 49,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 6.4 g 3-methylisothiazole in 100 ml dry tetrahydrofuran at -78° C. under nitrogen was slowly added 7.6 ml n-butyllithium (9.5 m). After 15 min. at -78° C., a solution of 12.0 g 1-bromo-5-chloropentane in 10 ml dry ether was added. The reaction mixture was allowed to reach room temperature where it was stirred for 90 min., then diluted with ether, washed with water and sodium chloride solution, and dried over sodium sulfate. Concentration and flash filtration (silica gel, 4:1 hexane/ethyl acetate) gave 6.5 g of 5-(5-chloropentyl)-3-methylisothiazole as a red oil, sufficiently pure (NMR) for use in the subsequent reaction.

Aufarbeitung

  1. customat -78° C.
  2. customto reach room temperature
  3. washwashed with water and sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationConcentration and flash filtration (silica gel, 4:1 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-bedb97a558e74664b101bea7b21f55e3
Quelldatensatz
uspto-grants-1990_07
Patentnummer
US04939267

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