Epichlorohydrin → 3-(3,5-Dimethyl-4-oxiranylmethoxy-phenyl)-5-(5-ethyl-thiophen-2-yl)-[1,2,4]oxadiazole

HRID 1094301Notizen

Reaktionsgleichung

[CH2:1]([C:3]1[S:7][C:6]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:18]=[C:17]([CH3:19])[C:16]([OH:20])=[C:15]([CH3:21])[CH:14]=3)[N:9]=2)=[CH:5][CH:4]=1)[CH3:2].[CH2:22]([CH:24]1[O:26][CH2:25]1)Cl>C(O)(C)C.[OH-].[Na+].C(OCC)C>[CH3:21][C:15]1[CH:14]=[C:13]([C:10]2[N:9]=[C:8]([C:6]3[S:7][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=3)[O:12][N:11]=2)[CH:18]=[C:17]([CH3:19])[C:16]=1[O:20][CH2:22][CH:24]1[CH2:25][O:26]1

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

A mixture of 4-[5-(5-ethyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenol (367 mg, 1.22 mmol) and epichlorohydrine (565 mg, 6.10 mmol) in isopropanol (20 mL) and 3 N aq. NaOH (6 mL) is stirred at 40° C. for 15 h. The mixture is diluted with diethyl ether, washed with sat. aq. NaHCO3 and water, dried over MgSO4, filtered and evaporated. The crude product is purified by CC on silica gel eluting with heptane:EA 9:1 to give 3-(3,5-dimethyl-4-oxiranylmethoxy-phenyl)-5-(5-ethyl-thiophen-2-yl)-[1,2,4]oxadiazole (123 mg) as a pale yellow oil; LC-MS: tR=1.15 min, [M+1]+=357.11.

Aufarbeitung

washwashed with sat. aq. NaHCO3 and water
dry with materialdried over MgSO4
filtrationfiltered
customevaporated
customThe crude product is purified by CC on silica gel eluting with heptane:EA 9:1

Quellen und Nachweise

ORD-Eintrag: ord-89196b5213394a1b88508c0ee932dcda
Quelldatensatz: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08133910B2

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