Aluminium lithium hydride → (2-(4-Methyl-3-(3-methylbut-2-enyloxy)phenylamino)oxazol-4-yl)methanol

HRID 1474010Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1474010
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[O:10][CH:11]=[C:12]([C:14](OCC)=[O:15])[N:13]=2)=[CH:4][C:3]=1[O:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[O:10][CH:11]=[C:12]([CH2:14][OH:15])[N:13]=2)=[CH:4][C:3]=1[O:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23]

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 68490366Ethyl 2-(4-methyl-3-(3-methylbut-2-enyloxy)phenylamino)oxazole-4-carboxylate

Produkt 1

HCID 86645049(2-(4-Methyl-3-(3-methylbut-2-enyloxy)phenylamino)oxazol-4-yl)methanolAusbeute 34,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of the compound ethyl 2-(4-methyl-3-(3-methylbut-2-enyloxy)phenylamino)oxazole-4-carboxylate (42 mg, 0.13 mmol) in anhydro THF (1 mL) was added to a suspension of LiAlH4 (10 mg, 0.25 mmol) in dry THF (1 mL) cooled at 0° C. under nitrogen atmosphere. After 2 h, the reaction mixture was quenched with H2O, filtrated, dried over MgSO4 and concentrated. The title compound was purified by flash chromatography on silica gel (hexane:EtOAc 1/1) to afford the product (13 mg, 34% yield).

Aufarbeitung

  1. customthe reaction mixture was quenched with H2O
  2. filtrationfiltrated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe title compound was purified by flash chromatography on silica gel (hexane:EtOAc 1/1)

Quellen und Nachweise

ORD-Eintrag
ord-be2b52f770e64ee2a0aab3d2beb22601
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018209B2

Notizen zur Reaktion

Wird geladen…