Tetrahydrofuran → 2-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethanol

HRID 2215207Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2215207
[CH:1]1([C:7]2[O:8][C:9]([CH3:16])=[C:10]([CH2:12][C:13](O)=[O:14])[N:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1COCC1.B.C1COCC1>CO>[CH:1]1([C:7]2[O:8][C:9]([CH3:16])=[C:10]([CH2:12][CH2:13][OH:14])[N:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 2723981Borane;tetrahydrofuranHCID 10857080(2-Cyclohexyl-5-methyl-oxazol-4-yl)-acetic acid

Produkt 1

HCID 108567262-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethanolAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

1.920 g of the above prepared (2-cyclohexyl-5-methyl-oxazol-4-yl)-acetic acid (8.60 mmol) was dissolved in 56 ml of abs. THF and treated at 0° C. with 21.5 ml of 1M BH3THF (2.5 eq.). The reaction mixture was then kept over weekend at ambient temperature. 3.5 ml of MeOH was added and the mixture stirred for 3 h at ambient temperature and for 3 h at 50° C. to liberate the free alcohol. Removing of the solvents i. V., followed by flash chromatography (SiO2, hexane/AcOEt=4/6) yielded finally 1.314 g of the title compound as colorless oil.

Aufarbeitung

  1. dissolutionwas dissolved in 56 ml of abs
  2. waitThe reaction mixture was then kept over weekend at ambient temperature
  3. customRemoving of the solvents i

Quellen und Nachweise

ORD-Eintrag
ord-dd2d681717be4f00bd6b834d8c247d5e
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109225B2

Notizen zur Reaktion

Wird geladen…