Water → 5-(4-Cyanophenyl)-3-hydroxymethyl-1,2,4-oxadiazole

HRID 54540Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 54540
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[C:11]([C:14](OCC)=[O:15])[N:10]=2)=[CH:5][CH:4]=1)#[N:2].O1CCCC1.[BH4-].[Na+].O>CO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][N:12]=[C:11]([CH2:14][OH:15])[N:10]=2)=[CH:7][CH:8]=1)#[N:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 199591483-Ethoxycarbonyl-5-(4-cyanophenyl)-1,2,4-oxadiazole

Produkt 1

HCID 199591695-(4-Cyanophenyl)-3-hydroxymethyl-1,2,4-oxadiazoleAusbeute 96,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 5-(4-cyanophenyl)-3-ethoxycarbonyl-1,2,4-oxadiazole (5.0 g) in methanol (50 ml)--tetrahydrofuran (50 ml) was added sodium borohydride (0.93 g) at 0° C. After stirring at 5°-10° C. for 1 hour, the mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was recrystallized from diethyl ether to give 5-(4-cyanophenyl)-3-hydroxymethyl-1,2,4-oxadiazole (4.0 g).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was recrystallized from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-008dbd1864a042c18c6448049da19547
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622976

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